Go Big, Or Go…Startup

big Fish Little Fish

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A common career advice question I get all the time is what the tradeoffs are between going to a startup vs. going to a big company. There are many things to consider and lots of “it depends” when it comes to where you are in your career, where you live etc., but when it comes to the general aspects of a startup vs. mature company, most of the situations don’t vary that much. I’ve done both, several times, so here’s a perspective on the tradeoffs based on my own experiences.

Startup vs. Mature Company

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(c) 2018 Julia B Austin

Putting aside for a moment industry and how you feel about the products the company is building (both of which are very important!), most of the differences between a startup vs. a mature company are pretty obvious. In a mature company, you will likely have more role models to learn from and stronger teams to collaborate with, a clear direction and a mature board. The role you consider may have a narrow scope, but could offer deeper learning and of course great benefits, compensation, etc.. You’ll also get exposure to what good (or bad) looks like at scale and possibly a nice brand for your resume.

Startups can offer a chance to do “all the things” which can be either a blessing or a curse depending on your interests. You may miss out on having peers to collaborate with, have to look outside of your company for mentors and role models or have limited budget to get stuff done, but you may get high value equity in exchange for lower than market-level pay. If you want to dig more into deciding which startup to join, I suggest Jeff Bussgang’s book Entering Startupland which goes deep on the different roles at startups and how to get your foot in the door.

Leadership

One thing often overlooked when considering a new job is the leadership of the company. Serial entrepreneurs will have a very different approach than someone who has limited real-world experience and mature company executive teams can be world class or “legacy” leaders who can’t move with the times. There are many tradeoffs when factoring in leadership into the decision process of startup vs. a mature company.

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(c) 2018 Julia B Austin

Startup founded by serial entrepreneurs: This can often be the best case scenario if you want to learn from those who have “seen the movie before”. They likely had no issue raising money and were selective on who their investors were and who sits on their board. They will know how to get the flywheel moving incited by past mistakes OR failures.

“When I started my fifth company I knew exactly how I wanted to build the team. So, on day one I hired a head of recruiting to get things off to a strong start. I also knew market adoption would be critical to fundraising so focused on growth very early on – before we even had a product!” – David Cancel, CEO & Co-Founder Drift

Serial entrepreneurs may also try to overcorrect in areas where they failed the first time, such as over analyzing or delaying decisions, being too conservative on cash flow or focusing too much on scalability too early in the product development process. If you’re interviewing with a serial entrepreneur, it’s always good to ask what lessons they learned in their last startup and how they’re bringing those lessons into their new venture.

“I joined Drift in part because I wanted to learn from the experience of the co-founders. They’ve seen it before so they anticipate issues, they know when (and how) to hire experts to level up the team, and they know what’s “normal” for a hypergrowth company. It’s the best of both worlds: you get the rollercoaster startup experience with some of the more measured leadership and strategic characteristics of a bigger company.” – Maggie Crowley, Product Manager Drift

Industry veterans doing their first startup: Founders coming from mature companies with no startup experience can have big company confidence, be great at hiring and leading teams, but lack scrappiness to get a Minimum Viable Product (MVP) out the door and work towards product market fit.

“At our first startup after a series of roles at large enterprise software companies, we tried to force a big company perspective on how we did employee feedback and reviews. We were too structured with this initially and quickly cut back to a more loose feedback and review process with our team.” Izzy Azeri & Dan Belcher, Co-Founders Mabl

They may also be too used to having teams of people and systems in place to cover the more mundane duties of running a company and don’t want to get their hands dirty. On the flip side, they often know how to implement those processes and know the people to hire to run them so once the flywheel is moving and cash is in-hand, they can get momentum quickly.

“Earlier in my career, I hired a small team within a large corporation that was scrappy and had entrepreneurial mentality. At my startup, I quickly realized the benefit of once having a corporation behind me when things weren’t working out. The impact of a bad decision or process was much greater with no safety net.” – Karen Young, CEO & Founder Oui Shave

Startup with limited leadership experience: Working with a skilled group of founders leading teams for the first time can be tons of fun. If you bring some experience to the table, it can be very gratifying to not only work from the ground up, but also work alongside these founders as they grow. However, it can be frustrating if you find yourself figuring out things on your own because there’s no one in the company to mentor you. These situations can be very rewarding if you’re patient and you can always get outside mentors and advisors if they’re not available at this type of startup.

“When we started, we got a lot of advice like: stay focused, don’t expand too quickly, be careful that experienced hires match your culture.  All good advice, but we discovered there’s no real substitute for learning the hard way. The lesson just doesn’t sink in until you feel the pain of doing it wrong.” Wombi Rose, CEO & Co-Founder LovePop

Mature company with inexperienced leadership: If they made it this far, they are either wicked smart, lucky or both! More likely they also have surrounded themselves with strong, experienced leaders, investors and/or board members. You can learn a lot from joining a company like this, but they are very, very rare! When companies scale too fast, they can also suffer from having people in roles that have outgrown their experience. Read more about the impact of Hypergrowth situations written by my friend at Reboot, Khalid Halim, for First Round.

Mature companies with experienced leadership: These organizations have all the standard things you’d expect. Probably more politics and process than you’d ever find at a startup, but the benefit of exposure to great role models and best practices can be invaluable. Sometimes, these bigger companies can also expose you to the “dark side” of leadership and processes which are also great learnings on what not to do in your next job or company you may start yourself.

Which comes first in your journey?

For those doing early career path planning and knowing they want to do both a startup and a mature company at some point, there’s always the question of which should come first. Hiring managers at early stage companies can get “spooked” when they see someone with too much time (5+ years) at mature companies; questioning whether the candidate will be able to transition to startup life. Not that it’s impossible, but it’s something to consider. For these candidates, I suggest highlighting any scrappy “ground zero” work they may have done at their companies to demonstrate they can handle ambiguity and take risks. I am also a huge (and very biased) fan of people who’ve joined companies early and scaled with them. They have learned a TON from those experiences and can often start scrappy, but know how to operate at scale. Win-win.

Conversely, someone with a lot of startup experience may have a hard time adjusting to mature company. A hiring manager at a mature company may question whether a candidate with only startup experience can handle a slower pace or won’t know how to navigate a complex organizational structure that requires political and communication savvy. You may have to sacrifice title and maybe some salary to get a foot into larger institutions who may view your past role, which may have been very senior at a startup, to being pretty junior if those around you have decades more experience. However, I always find those with startup experience can be invaluable to a team that needs to be shaken up, take more risks or explore new ground. Often, those who sacrifice title and pay when they joined, make it up fast as they move up the chain in a larger organization.

There’s no right or wrong place to start. A lot depends on how you define your skills and how willing and patient you are in either case to adjust. Much can depend on who hires you and their management philosophy. I’ve seen some people bounce between both types of situations over and over, some that just can’t handle startup life, and others who have startups in their DNA and should just stick with that world 🙂

“At a startup, every job matters and you can see almost daily that you are creating something that wasn’t there before. You have the ability to learn quickly and have a fast feedback loop to let you know how you’re doing. It’s very different working at an established company vs a startup, but you can learn a lot at both – you’ll just learn very different things.” – Rebecca Liebman, CEO & Co-Founder LearnLux

Questions To Ask

Regardless of whether you are a seasoned veteran or fresh out of school, as you ponder whether you want to join a startup or a mature company here are some final things to consider:

  • What tools do you want to add to your toolbox? Will the role allow you to hone skills you already have or add new ones?
  • Who do you want to learn from, and how do you want to learn? You can learn from experienced colleagues and mentors, but having bad role models can also teach you a lot about what not to do. Similarly, if you are an experienced hire coming into a company started by inexperienced founders, you may want to learn by mentoring or teaching these young leaders. Taking the skills you’ve developed over your career and applying them to a new situation in itself can be a very enlightening experience.
  • Who do you want to work with? How important is the size and culture of the team you’ll work with? Remember, you’ll probably spend more waking hours of the day with these people than anyone else in your life – regardless of the size and nature of the company you join.
  • What do you value? At the end of the day, love what you do and decide what role will allow you to maintain the integrity of who you are and who you aspire to be!

Do you have other tips on how to decide whether to join a startup vs. a mature company? Please share in the comments!

Mastering The Team Meeting

No matter how much we hate going to meetings, there’s a generally accepted best practice that teams should meet with their manager as a group on a regular cadence. More often than not, I hear leaders and/or their staff dreading their team meeting. Instead of these meetings being the least favorite time suck of the week, wouldn’t it be great if these were the meetings we looked forward to? That we felt it was time well spent with our colleagues and added value to our roles in some meaningful way?

There’s no reason you have to suffer or make your teams suffer through another tortuous hour or more. A while back, I shared protips on Mastering the 1:1. Now, herewith my tips on Mastering the team meeting…

Meeting Purpose: Set a clear purpose for your team meeting. What do you want your team to get out of the time spent together? Do you want them to stay informed about larger topics in the organization? Get to know each other and their respective work better? Whether you are rebooting a long standing meeting or you are a new leader of a team gearing up for your first routine meeting, talk with your team members about what they want out of the session. This time is much more about their needs than yours, so align the purpose with their needs. A fun way to get this dialogue going is to ask each team member to complete this sentence: “My favorite meeting of the week is my manager’s team meeting because……” What would they say?

Agenda: I am a firm believer that if a meeting is important enough to have, it should have a time-boxed agenda and always be followed up with notes and action items (“AIs”). Protips on setting the agenda:

  1. As the team leader, you should solicit 1-2 “hot” topics per meeting from your team. I recommend you do this no more and no less than 48 hours before it is scheduled so ideas are timely and content is fresh. Topics should not be tactical – that’s what stand-ups and 1:1s are for. Instead, focus on strategic discussions and information sharing. On the latter, do not make it a status reporting meeting. Information sharing could be a product demo, or draft of a presentation someone is preparing for a conference or a preview of a big announcement to solicit feedback before it goes out.
  2. Always send the agenda for the meeting 24 hours in advance. This sets expectations and ensures no surprises and attendees are well prepared.
  3. Prepping for the meeting should take less than 15 minutes. Solicit agenda items – prepare agenda – communicate agenda. Long slide decks and spreadsheets created just FOR the meeting is a total waste of time. If those materials already exist and can add value to the discussion, then owners of said content should A) share these materials ahead of the meeting for pre-reading and B) bring said materials with them and be prepared to share them at the meeting.
  4. Lead by example for your team and read all materials sent in advance before the meeting. If you have not read them, no one else will and again, you’re wasting people’s time. If you’re prepared, everyone else will be prepared.
  5. Finally, always carve out 10 minutes at the end of the agenda to take a pulse on your team. My method is “share thumbs at one”. Three, two, one and on one have everyone in the meeting give a thumbs up, down or sideways. I do a quick read of the room and video screens to gauge if we’re trending in a particular direction and, if so, take time to discuss. People feeling really up? Share why! People feeling down? How can we work together to make things better? This simple, transparent, way of sharing how the team is feeling is a great way for you to lead and for them to support each other. I also find doing this at the end vs. the start of a meeting tends to be a better read because no one is bringing the stress from a prior meeting into their pulse check.

Meeting Engagement: No one wants to listen to a monologue at the team meeting and no one wants to be in a meeting with other people who are checked out. Several protips to avoid this:

  1. Ask 1-2 members of your team to take the lead on the hot topics in each meeting. They do not need to be the experts on the topic, just the topic leader. This includes having them facilitate getting pre-reads to team members ahead of the meeting. The more they have ownership in a topic, the more engaged they’ll be.
  2. The team’s leader should not speak more than ⅓ of the time throughout the meeting. Other than updating your team about broad company topics, your job is to facilitate the discussion and LISTEN. If you’re a bad facilitator (not every leader’s strong suit), then appoint or bring someone in to facilitate. I’ve seen everything from EAs and HR leaders to program managers serve as facilitators of meetings – they keep the meeting on topic, on time and pay attention to the room. I don’t recommend one of your team members be the facilitator – they are there as an engaged participant, only.
  3. READ THE ROOM. Are people reading their email, checked out on a remote phone or video line or rolling their eyes at each other (visibly or under the table on their cells via text…)? Pay attention to what’s happening in the meeting and pause if you see this kind of behavior. If you’re losing people, you’re wasting everyone’s time and you’re costing the company money. (do the math, the average team meeting can cost a company thousands of dollars every week!). Tell people to put their phones or laptops away if they are checked out. Ask people called in remotely if they have anything to add to the conversation. Pull them in. If the topic is falling flat, be direct and ask why or solicit suggestions on how to make it more engaging. E.g., budget discussions are rarely engaging so even a simple “bare with me as we get through this” can go a long way.
  4. Have fun! It’s great to start a meeting with a funny anecdote or personal story to wake up the room. Maybe someone on your team has a good customer story or had someone on their team get a “win” worth sharing. Perhaps you have a fun personal story to share that shows your human side. Keep it light where you can, but serious during some of the tougher topics (budget, staffing, etc.). This fortifies the culture of your team both inside and outside of the meeting.

Tactical Stuff: When you meet and who goes to the meeting is just as important as the agenda and the content. Protips:

  1. Timing: Got a distributed team in multiple timezones? Find a time that’s mutually convenient for all team members. Do you find the meetings always run over? Schedule it for an extra 30 minutes and if it ends early, everyone gets time back – you’re a hero. Does the team have family responsibilities in the morning or after work? Don’t schedule the meeting such that it disrupts their lives outside of work (if it can be avoided). I also generally discourage team meetings on Mondays (frequent holidays/long weekends means rescheduling or skipping too often) and Fridays (long weekends and if hard topics, no time to debrief/process offline before the weekend).
  2. Decision making: If a meeting has >8 people attending, it is an “information sharing” meeting. Less than that, and decisions can be made at the meeting. If you have a team greater than 8 people, tee up decision topics for discussion and, unless it’s a layup, take the actual decision off line. Otherwise, there are “too many cooks”.
  3. Assign and rotate a note taker at every meeting. You and/or the facilitator cannot read the room and take notes at the same time. Further, by rotating the role across your team, you foster engagement and get fresh perspectives on the meetings each time. Notes should be distributed no later than 24 hours after the meeting while things are fresh. Always call out AIs with owners and deadlines in the notes.
  4. Guests: An agenda should always build in intros for guests and should be time-boxed for cameos. For example, if the head of HR is a guest at your meeting to talk through the next review cycle with your team, the team should know that person will be there and why. Further, unless there’s scheduling trickiness, have guests come at the start or end of the meeting so as not to disrupt the meeting with people coming and going throughout. My personal preference is guests at the start. Then we get into our regular routine.

Most important, don’t set it and forget it. If you do change things up, be clear on why you’re doing it and give it time to settle. Starting or overhauling your meeting process won’t necessarily show positive results the very next meeting and changing it too often will not only cause unrest with your team, but can create distrust if the rules of engagement keep changing. Have at least 4-6 meetings for a new routine to set in and then evaluate whether the changes are effective and adjust as needed. Solicit feedback from your team regularly too – after all, it’s their meeting!

Do you run a kick ass team meeting? Or, do you have ideas on how to improve the team meetings you attend? Share your protips in the comments!

The War For (Diverse) Teams At Early Stage Companies…and Beyond

Note: Diversity is a term used 30+ times in this piece and refers to all types of diversity, beyond just gender.

In 2004, there was a post-bubble burst resurgence of well funded startups and VMware, like many other companies in the Silicon Valley, was struggling to compete for talent against Google, Yahoo and others in their space. The hot conversation in the weekly e-staff meeting in Palo Alto was about maintaining the bar and hiring the very best talent they could find. This was well before diversity and inclusion was trending as a hiring pain point. There was a war on talent.

To combat this war, the leadership team at VMware got creative. There was an urgency to bring on talent and just competing on compensation and equity wasn’t enough when that talent pool itself was sparse. So, leveraging ties to several of the team members’ east coast roots, they tried an experiment and opened an office in Cambridge, MA.

As the Site Director hired to build out that office at the start of 2005, I was charged with bringing on at least a dozen engineers by the end of the year. I had strict guidance on who to hire first;  the first six hires had to be at least a Staff level engineer, which at that time was like a Principal at most other companies. Even though we were desperate to bring on more talent, the leadership team insisted we still keep the bar high. There were no compromises – hire the best, no matter what.

By the end of 2005, we ended up hiring over 20 seasoned engineers and were well poised to scale that location with more junior talent and expand into other regions across the globe. It was a hard push to win the war, but we won it and many would say that getting scrappy, maintaining the bar and taking risks outside of Palo Alto to hire great talent was one of the key factors that led to VMware becoming the multi-billion dollar success story it is today.

Getting Scrappy And Taking Risks To Create Diverse Teams

Flash forward to 2017, and the talent war is still on, but it’s not just about hiring top talent, it’s about hiring for diversity. There’s plenty of science to prove that diverse teams are what separate average companies from the big success stories. Once there’s diversity in teams, you attract more candidates from underrepresented groups. But there is a catch-22 when companies and teams with no diversity can’t hire candidates from underrepresented groups, in part, because they have no diversity in their current teams!

I was at an event recently where I sat in a breakout session about diversity and inclusion where most of the fifteen or so participants were white, male, CEO-Founders of very early stage companies. These leaders were complaining that despite best efforts, they were not able to find/hire qualified, candidates from underrepresented groups for their open positions. Investors were on their back to meet deadlines and reach revenue goals and the push for building diverse teams was not a high enough priority to push back. They had to hire the best talent they could find, and get coding!

But what if that talent didn’t exist? What if it was 2004 and there were no engineers to hire, never mind engineers from underrepresented groups? How do companies, like VMware did back then, combat this war vs. becoming complacent? What can companies do today to be creative, continue to scale, and develop a diverse team? What if CEOs, their leadership team and their boards held the line on diversity metrics, no matter what?

Starting From The Top

A company that is committed to diversity must demonstrate that commitment from the top, down. CEOs set the tone for the organization’s culture by demonstrating a commitment to diversity and inclusion. They don’t just say they care about the problem and acknowledge the importance of solving it, but they force it to happen. VMware’s founding CEO, Diane Greene, was adamant that we hire only the best talent from day one, and CEOs today need to do the same when it comes to hiring diverse talent.

One of the most compelling reasons for any strong candidate to join a company is knowing there’s diversity at the senior most levels. Having Diane at the helm played a huge role in my decision to join VMware. She was a role model and inspiration to everyone at the company as she balanced the complex demands of scaling our business with her family and other commitments outside of work. We were not only inspired to follow her drive and passion for the business, but the company naturally attracted other strong, candidates because of her leadership.

Whether you are an early stage company, mature business or even just a growing team within a maturing business, committing to diversity at the top is critical. Here are some suggestions on how to do that:

  • The founding team: Diversity does not just have to exist between your co-founding team, it should be among your first hires, your advisors, customers and/or friends of the company. The more diverse the team, the more likely you will be to attract new team members from under represented groups. Introduce prospects to these company “community” members to begin to demonstrate your commitment to this metric at the start. For example, I frequently join interview panels for early stage companies I advise to ensure not just a great hire, but to add diversity to the panel itself.
  • Set and hold the diversity bar for leadership hires: Don’t say “it would be really great to fill the next senior role with a diverse candidate”, rather make it mandatory to create a diverse organization. “We will not hire another manager, director, VP, etc. unless they bring diversity into our team.” Get scrappy and go hard to build these teams (see below). Stop looking for just culture fit and homogenous pattern matching and seek those different than you – they are sure to be additive to your organization beyond just their skills and experiences. Yes, it may take longer to find that person, but hold out for it – it’s worth it!

Note to VCs & Board Members

It is great to see so many VCs and board members stepping up to foster diversity in their portfolios. They are committing to invest in more women founded companies, hosting “diversity events”, making the Decency Pledge and some are creating special funds for diverse entrepreneurs. I believe many VCs are sincerely interested in this effort and not just creating PR tactics to position firms to appear supportive. While those efforts are important to further the cause (don’t stop doing them!), I challenge them to set the bar higher; implementing hard accountability metrics for diversity in their firms and in their portfolio companies. To not be complacent in the reality that it’s “hard to find qualified  candidates from underrepresented groups”, but rather force change to happen. Here are a few suggestions:

  • Mandate that your partnership be a diverse team. Studies continue to come out on how diversity in investment teams have stronger exit outcomes. Get scrappy and find ways to build diverse teams for your firms. The more diverse your team, the more likely your firm, will attract a more diverse group of entrepreneurs into your deal flow. And don’t stop at one – keep forging ahead and strive for a more balanced group of partners; a token diversity hire isn’t enough. Also, each partner from an underrepresented group on your team allows for more diversity on your portfolio companies’ boards. While there’s great debate on whether there’s a direct correlation with diversity on boards and company performance, it is a sure thing that diverse boards add new perspective and new ideas to help the organization succeed.
  • Refuse to fund a non-diverse team (!). Yes, you may have to get your LPs to sign off on this, but many LPs are now pressuring the funds they’re in to push harder on the diversity front. So, take the lead, be proactive and tell them you’re holding the bar. Even if it means an initial slow down on deal flow and longer lead times to exit. The data proves that those investments are far likely to pay off in a bigger way than the non-diverse team investments you’re making today.
  • Set your portfolio teams up for success and help find candidates from underrepresented groups for your investments. Extend runway with a bridge loan or other means until the company has had at least six months to try to shore up their team. Make this a priority of your firm. This too is likely to improve deal flow if you offer this type of support to entrepreneurs as many entrepreneurs are not even coming to you because they don’t have the requisite co-founder, never mind a co-founder/founding team that is diverse.
  • Cover the cost to augment teams during the recruiting process. Not only encourage your portfolio companies to bring in consultants/contractors from underrepresented groups as part of their core team until they demonstrate diversity in their teams, but pay for it! Invest in your teams beyond the equity round.
  • Note to Founders: Depending on urgency to raise capital, you might consider refusing to take money from funds that don’t walk the talk – will your board be diverse? Would non-diverse investment group allow you to fill their board seat with an alternate who brings diversity into the board? The more senior candidates you are courting to join your company will examine board composition carefully – especially if your investors play an active role in the day-to-day of your company (It happens more than we think!). How hard are you willing to work to get a diverse board? Also consider creating a seat for an independent board member from day one to be used if needed to round out your team.

Beyond The Leadership Team And Investors

How are you set up to source for and hire diverse teams? Are you looking in all the right places? In 2015, I wrote a whole primer on hiring for startups (much of which is also applicable for later stage companies), but here are some specific tips on getting creative on hiring for diverse teams:

  • Diversity in your interview panel: Most hiring managers these days know it’s ideal to have a diverse interview panel to help sell a candidate on the role and company, but if your team lacks diversity, consider augmenting the interview team with diverse “community” members – either from other teams in your company or by inviting board members, advisors, friends of the company, etc. to participate. More good info on the hiring process for diversity here.
  • Join, sponsor or network with diversity orgs: There are countless non-profit organizations that cater to diversity hiring causes. For example, joining the National Center for Women in Technology’s Entrepreneurial Alliance which is designed for both startups and incubators/accelerators, provides access to job forums, invitations to their events and connections with over 600 other membership companies. Blackengineer.com has a jobs board, as does lgbtconnect.com. There are loooong lists of other organizations you can tap into to support diversity hiring efforts here, here and here.
  • Bring on Diverse Contractors: To me this is a win-win. You can start getting some work done and having diversity in the office can allay concerns when members of underrepresented groups come in to interview. I’ve heard countless stories of a candidate going for an interview and saying “the whole office was dudes or all white” …you get the visual. I’ve also heard many stories of contractors who fall in love with the company they’re working with (and vice versa) and join full time! (and as noted above, maybe you can get your investors to pay for it!).
  • Never miss the opportunity of a passive candidate: So many companies fail to build diverse teams because they wait for applicants vs. seeking out great people. Troll LinkedIn, go to meetups related to your company’s area, hire sourcers to look for great candidates who may not even know they might want a change until they get a call from your company! Don’t wait for these candidates to come to you.

The First Diverse Hire

Once you reach success and start to hire diverse team members, remember, for many of them, they may be the first one – whether it’s at your company as a whole or perhaps just in one team. There can be an ominous feeling when one thinks they’ve been courted or hired as the token diverse candidate/employee. What will you do to ensure that they are set up for success?

  • Acknowledge the problem from the start. The first time you diversify your team, especially for a small company, the individual will know they are bringing diversity to the table. Speaking from experience, it’s fine to call it out, as long as it’s clear that this is not THE reason they are in consideration. Needing a strong technical leader, or someone who has specific domain expertise is the priority, diversity is simply a value add to the team/company…but don’t dwell on it.
  • Consider how you operate today and whether there are any conscious or unconscious biases towards the current homogeneity of your company/team. Are there activities that happen at work or after hours such as fantasy leagues, spa trips or perhaps even non-family friendly activities that keep the first diverse hire from feeling comfortable or the outlier? Does your office decor offend or intimidate? Carefully examine how your company culture, rituals and environment is setup to be as friendly as possible.
  • You’re not done – the first hire that creates diversity in your team should not check a box and then you move on. Keep at it and for God’s sake please do not make that hire the ambassador for all future diversity activities! It is still the hiring manager/leadership team’s responsibility to keep the momentum.
  • Finally, focus on retaining those great hires.

Make diversity a priority. Hold yourself, your team, your investors and your board accountable. Set standards, get scrappy and change things for the better.

This is a war on for diverse teams. Treat it that way.

Reply in the comments if you have other creative suggestions on how to win the war on creating diverse teams.

Opening Doors & Taking Action

open doorsAs the news unfolded in the past week over Susan Fowler’s recent blog post about her experiences at Uber, I have been thinking deeply about finding my voice on the matter. I recalled the countless times I had been harassed and never said a thing to anyone, let alone the HR rep at whatever company I was working at the time. I have dozens and dozens of stories of inappropriate, sexually charged, comments from colleagues, winks, suggestive touches, crass jokes, and pictures shared with me that I wish I could unsee. I never called them out.

Fear of gaslighting – being accused of being oversensitive, crazy, blowing things out of proportion – is probably one of the top reasons for not reporting the umpteen incidents employees experience in the workplace. It seems no matter how high we climb the corporate ladder, we still hold back. Whether it’s gaslighting, possible retaliation, or as in Susan Fowler’s case, being totally ignored, we doubt we will be heard.

On those rare occasions when we are heard, those who fall victim to bad behavior or blatant harassment are often “handled” quietly, if at all. Issues are swept under the rug before anyone knows. So, regardless of whether the bad actor gets a warning or more severe action is taken, no one else learns from this lesson. Organizations and leaders desperate to protect their reputations and avoid litigation make it go away a fast as possible. Perhaps those who helped “clean it up” get a reality check, but as long as there is no exposure, no public shaming, no admission of guilt, we will continue to see situations like Ms. Fowler’s persist.

It was a bold move for Ms. Fowler to publicly share her story about Uber and its leadership team’s lack of attention towards her situation. The ubiquity of Uber, and attention the company is already getting in other forums, certainly gave fuel to this issue, but this is not just about tech companies gone bad. It was a rallying cry for leaders at any company, big or small, to not only open the doors for employees to be heard, but to make it clear that crossing the line is no longer tolerated and when it is crossed, action is taken.

Opening Doors
Building a culture of open doors is not just about telling employees “my door is always open,” but actually opening that door. We had a thoughtful series of conversations on this topic at DigitalOcean (DO) over the past week. At our company all hands, we emphasized a zero-tolerance for any harassing behaviors that make our employees feel unsafe and our CEO and I both committed that, while we want people to talk with their managers and our People team first, we are 100% available to talk with any employee who is uncomfortable and prefers to talk with either of us about any issue.

Our commitment to our employees this past week has been well received, but executives making statements about their open doors is only part of the equation. Opening doors is also about ensuring a safe and inclusive work environment by proactively mitigating issues. Ensuring a safe work environment involves everything from setting policies and guidelines to conducting cross-company training beyond the online course we are required to click through when we start a new job.

studentdiscussion_250One of my former employers offered a training using situational role playing to develop understanding and empathy for those who may not appreciate the severity of certain actions. It was an invaluable exercise and we do something similar with the unconscious bias training we provide to all new employees as part of their on-boarding at DO. We’ve found by raising awareness of these behaviors in realistic settings we can do a lot to set clear expectations on what acceptable and unacceptable is, and make people more aware of their impact on others.

If you see something, say something.
Despite proactive efforts, open doors, trainings and policies, harassment still happens. Sometimes, it’s an innocent mistake where a young/inexperienced employee just doesn’t realize they’ve said something wrong. Sometimes, it’s an experienced executive who’s never been called out thus doesn’t appreciate the impact of their behavior. Regardless, we cannot stay silent.

I believe every manager is accountable for reporting any incident that they observe or is reported to them as soon as possible. I also believe it’s every employee’s right to know that their company is taking action to ensure a safe workplace. However, because of corporate policy and privacy protection, we often lack the transparency of how organizations are handling situations and whether they are operating a safe place of work. We cannot, for many reasons, publicly call out every person who crosses a line, but there could be methods(*) to get ahead of this such as:

  • Providing a safe forum for any employee to report an incident they’ve experienced or observed.
  • Tracking anonymized incident data to look for trends including frequency of issues and resolution timeframes.
  • Implementing and broadly communicating Employee Assistance Programs (EAPs) that provide hot lines, advocacy and legal counsel.
  • Internal or even public communication on a company’s performance regarding harassment situations. Imagine a world where companies own unfortunate situations and say how they are resolving them and share improvement data. Scary as that may sound, I bet that if more companies shared this information, the trend of incidents would go down.

The beat goes on…
Whether it was in Twitter or in an intimate setting among friends, Susan Fowler’s story is not the first we’ve heard like this nor will it be the last. We need to continue to bring these topics front and center and commit to continuous improvement in the workplace. I’d love to hear how other leaders are handling this topic at their companies. We all benefit from learning from each other, so please share your stories in the comments.

(*) These are just suggestions, I leave the real policy and program design work to the experts 🙂

The CTO to VP Engineering Fork

bfa_code-fork_simple-black_512x512There comes a time in every scaling tech start-up’s life when an engineering team begins to show signs of needing help. The symptoms can include lost velocity in releasing new products/features, attrition or morale issues, fragile code or lack of innovation. I frequently hear CEOs and founders say “we need a new CTO” or “should we hire a VP of Engineering?”. But what does that really mean? A title is one thing, but the skills necessary to cure the symptoms is a whole other challenge.

Most tech startups have someone serving as CTO — whether it is one of the co-founders or a first senior hire. The role of the CTO is not straightforward and as a company scales, it’s unreasonable for that role to be the end-all-be-all. In the early days of a startup, the CTO is often the chief cook and bottle washer for all things technical. She is coding, serving as the de facto IT person and project manager as well as meeting customers alongside the CEO and helping with hiring decisions. She is expected to be deeply technical and often a domain expert. Firing on all of these cylinders may meet your company’s needs in the short-term, but quite often, there reaches a point where your CTO is no longer being excellent at what they came to your company to do.

In my experience, there tends to be two types of CTOs that evolve as a company grows:

The Evangelist — The shameless promoter of your product, this CTO is out on the road meeting prospects, existing customers and partners and marketing your product. At the same time, they are gathering valuable insight into your product, its pain-points and understanding how it compares to the competition. They are mindful of industry trends and the ecosystem of which your product belongs. They are the ultimate voice of the customer and are keenly aware of the product priorities. They set the vision for the “.next” of your product and the long-term roadmap. They may have once been a coder and understand the basics of your technology architecture. They can go head-to-head with other technology leaders in your space and represent your company at technology conferences. They also tend to be a recruiting magnet for engineering talent.

This CTO works hand-in-hand with the CEO and sales and marketing leads to set the strategy for the company — from market direction to the operations and scale of the business. They are financially savvy and comfortable presenting to and working with your Board of Directors.

The Expert — Often a domain expert or technical guru, this CTO is heads down with your engineering team ensuring your products are built to perform at scale. They may code, sit in code reviews, and mentor junior engineers. They are either designing your underlying architecture or at the very least leading that conversation and signing off on proposed plans. Also talent magnets, they attract senior engineers who wish to learn from this CTO’s experience. They may be key contributors to the open source community, prolific in filing patents, publishing technical papers and speaking at technical and academic conferences. While they enjoy meeting customers and value the insight from those meetings, they prefer more intimate meetings with technical members of customer teams and whiteboard sessions to brainstorm solutions vs. “selling” your products.

This CTO works closely with the sales and support team and often leaves the company strategy and growth discussions to the CEO and other leaders of the organization. They have an opinion on where the company should go, and they’re not afraid to share that, but they leave the details up to “management”.

The VP of Engineering

In both cases above, it’s rare when one of these types of CTOs is also a master at execution. This is when it is important to have a VP of Engineering (VPE). While a VPE can often be someone who can serve as a voice of the customer, be a technical expert and/or represent the company in technical forums, the VPE’s focus is on GSD. Key characteristics of a VP of Engineering are:

  • Process oriented — highly organized around priorities, velocity, quality and meeting deadlines. They have strong project management and communication skills.
  • Great at hiring — pattern matching skills for not just technical expertise, but for people who are collaborative and mission-driven. Knows how to ID the prima donna engineer from the eager-to-learn engineer and when to say “no” even with a great looking resume. Team fit is paramount to success.
  • Great at growing their team — this isn’t about going from 10 to 40 engineers. This is about career development. They’ve got a track record for bringing junior engineers into an organization and developing them into technology leaders and domain experts. Their former engineers have followed them from company to company because they are great to work with. They know how to have fun, but also how to appropriately push a team towards meeting a deadline with urgency and not burn them out.
  • Challenges the status-quo — they won’t just keep building what the co-founders started, but will question both the what and the how. They understand the impact that technical debt can have on the long term scalability of your products. They also know how to tune processes without overkilling the company with process. They are motivated to deliver products and features that customers not only need, but love.
  • Not afraid to get their hands dirty — they lead/attend code reviews, can code if there is an emergency, enjoy tinkering with competitors’ products to understand advantages/challenges of your own products, and appreciate the fine art of squashing bugs. They come in early and stay late when there’s a deadline — even if it’s to make sure engineers are getting food and coffee.
  • Strategic thinker — while a VP of Engineering may not be at the the table deciding the fate of the company, they are part of the discussion. They understand tradeoffs of time-to-market vs. quality and value the need to get a MVP out the door to garner customer feedback early on. They may push for a product or feature, but also respect the larger vision of the roadmap and know when to let go of something that isn’t a priority — in fact, the really good VPE’s kill things sooner than a CTO or CEO may like for the sake of velocity and GSD.

When you’ve decided it’s time to fork that technology leadership role and have both a CTO and a VPE, look for someone eager to create a partnership. Someone who prefers to lean into GSD and growing teams and who values the technology leadership, vision and evangelism of your CTO. Be leery of career CTOs who seek a role as VPE at your company — they may say they’re willing to be in charge of GSD, but could easily step on your CTOs toes. Look for examples of past engineering leadership roles as managers or tech leads. Also look for measurable achievements like improved velocity rates, quality improvements or hiring/team development metrics. Those are telltale signs that you’ve got a solid VPE candidate.

Sometimes it takes a lot of soul searching for a founding CTO to realize they’re not serving the company well around VPE-types of activities. I’ve seen plenty of CTOs worried that with a VPE on board, they’re not sure what’s next for them at the company. I’ve also seen CTOs excel when partnered with a great VPE where they can set the vision and execution strategy in tandem. Fortunately, I am lucky to have such a VPE on board here @DigitalOcean — as well as two awesome Engineering Directors with whom we partner to drive our technology roadmap.

Have you struggled with the CTO to VPE fork? Share your experience in the comments!

Scaling Another Rocket Ship: Hello DO!

Every once and awhile, I meet a company so exciting, I can’t sleep because I’m thinking non-stop about its potential to scale, massively. Fortunately for me, I ended up joining two of them that turned out to be great success stories and I think I just found my third. Starting this month, I am joining the ranks at DigitalOcean as their CTO.

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Anyone who knows me well would agree that as much as I am an organizer and planner, I am also a risk taker. I love diving into challenges and creating results that require skill, agility and building relationships. While business savvy and technical skill are paramount to growing a successful tech company, understanding the human element and building high performing teams is what separates the good from the great.

In 1999, with a three year-old and an infant, I quit my healthcare IT job to go to Akamai to help them get organized before our IPO. Most of my friends and colleagues thought I was nuts, but I was hungry for bringing order to chaos and building something that made an impact. My three years at Akamai were among the toughest and most rewarding years of my career. We created the world’s first CDN for businesses and turned it into the backbone of the internet. The teams I led and partnered with were some of the smartest and coolest humans I’ve had the pleasure to work with. We pulled all-nighters together, cried together when we lost our CTO-Founder Danny Lewin on 9/11 and still celebrate the company’s success together at our annual “Akamai Pre-2002’ish Employees” reunion.

In 2005, I landed at VMware right after the EMC acquisition to help them figure out how to run a global engineering team. I took a leap of faith that we would not get fully absorbed into EMC (which was their MO at the time) and that I could help build another company made to last. What I found when I interviewed at VMware was the same good vibe I had at Akamai. Super smart people, fun, passion and humility…and of course, a wicked cool product. I still remember my final interview in Palo Alto – a last minute “Diane Greene would like to meet you” – that threw me for a curve. I was pretty frank with Diane that I wasn’t sure I could balance my role at VMware with three small children. She assured me that VMware would make it work, and they did. Both my career and the company flourished over my eight year tenure at VMware. When I joined the company, we had just over 800 employees and around $200M in revenue. Today, it boasts close to 19K employees and 2015 revenues were $6.57B. It was an incredible ride to help scale something that spectacular.

When I left VMware in 2013, I felt very lucky to have been part of two incredible rocket ship stories in the technology industry. After much soul searching around “Julia.next”, I settled into the startup ecosystem in Boston. I became a mentor at TechStars and recently began teaching a Product Management course at Harvard Business School. Until recently, I was fairly certain this was the tail end of my journey, but something was gnawing at me that I had at least one more in me. One more amazing rocket ship I could help scale.

Over the past few years, I’ve made a few investments and became a formal advisor to the founders of several local startups. It was one of these founders who introduced me to Moisey Uretsky, DigitalOcean’s co-founder and Chief Product Officer. For those who don’t know Moisey, let’s just say brilliance and tenacity is an understatement. Despite my protests against working with a company in NYC, Moisey convinced me to come to DigitalOcean HQ back in January to meet his equally brilliant and tenacious brother and co-founder-CEO, Ben, and get to know the business. One visit became several and within a matter of a few weeks, I was fully enamored and signed up to advise the company.

During my early work with the DigitalOcean team, my instincts told me that this is going to be another winner. It is beyond impressive how, in just four short years, DigitalOcean has built such a strong platform and community. Ben, Moisey and I – along with the other key members of the DigitalOcean leadership team – began to work together to forge a partnership that will enable us to super-scale this company. The achievements we’ve made to grow the business so far left me unable to resist the temptation to join full time to help take it all the way. So now here I am, honored and excited to be DigitalOcean’s new CTO.

So what is it about DigitalOcean that gets me so excited?

In addition to our tremendous business growth, strong culture, talented team and impressive list of investors, the most striking is the simplicity of DigitalOcean’s features that developers love. We let developers create, automate, and manage a robust cloud server infrastructure out of the box with floating IP addresses, shared private networking, tier-1 bandwidth, team accounts and SSD hard drives which all come as standard. And all of our services can be provisioned in as little as 55 seconds with a plan for as low as $5 a month.

I am continuously blown away at the reaction I get from people in our industry who hear I am working with this company.

“I love how easy it is to spin up a Droplet to build software!” – MIT graduate student building software for his own startup

“I have 6 Droplets of my own!” – Boston VC

“Their tutorials and community engagement is the best in the industry” – Engineer building a neuroscience application

“DigitalOcean gets developers – they give us what we need with no BS” – SaaS application developer

In addition to our core feature offerings, our multiple data centers around the world and a 99.99% guaranteed uptime enable companies to build and scale robust SaaS applications. Even more exciting is what’s to come. Our storage capabilities will begin to roll out this summer and what follows is a list of features that developers building production applications will surely love. Because at DigitalOcean, it’s all about love…

This is going to be another incredible journey of risk, opportunity and balance for me. We are an organization that values learning and what better way to hold that true than to continue teaching my course at HBS (fear not, @teisenmann & PM101’ers!). And, while I’ll certainly be spending a lot of time at our HQ in NYC, I will remain living in Cambridge and to continue to be an active member of the Boston area startup community.

Finally, I am hiring! We’re looking for amazing talent across the company. Check out our current career opportunities both in and outside of NYC.

Will DigitalOcean be another massively scaling rocket ship ? I’m pretty bullish about it. So check back here soon for updates on how it’s going!

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Adding Value By Transforming Your Business

business-transformationIn addition to creating a new company that is disrupting the status quo, many founders are also challenging the old norms of how businesses operate in order to add value. When you are struggling to raise capital, hire, and scale your business, is there time and energy available to also rethink how you do business in general? How much effort do you want to put in to stand out as a company not only creating something spectacular, but also a company that differentiates itself as an employer? What truly matters in the end is whether that transformational effort adds value.

In 2012, the gaming company Valve published their novel Employee Handbook  which outlined their organization structure (or lack thereof). Valve challenged the notion of having assigned projects to work on or managers to report to. Many other companies have taken similar approaches not only to attempt to operate more efficiently, but also to attract and retain talent by differentiating their companies from the mainstream.

Whether or not the super flat organization or self-directed projects works, these companies have challenged the standard on how business are “supposed” to run. One could argue that these attempts to be different are distracting and time consuming when the work just needs to get done. However, by taking a chance at doing something different, not only are they attracting new talent, these companies are fueling creativity and innovation across their organizations.

Transforming your business doesn’t always have to be time consuming or distracting. The company Amplitude challenged how businesses handle equity compensation by extending the company options exercise windows to TEN years vs. the standard 90-day window most companies offer. Amplitude also helps employees understand the complexity of their equity plans by outlining in detail the possible scenarios and potential outcomes of their particular grants. The message here is A) you add value to this company and should benefit from it well into the future and B) we want to be sure you fully understand that value as an important member of our team. I imagine neither the window extension or transparency tactics were very time consuming or distracting to implement (well, perhaps the former took some selling to their investors!), but they certainly make this company stand out as an employer and innovator.

Most recently, eShares has stepped up their game by revamping the offer letter. CEO Henry Ward decided that, being in the business of equity management, they should excel in helping job candidates and new employees fully understand what it means to have options in their company. There’s even more to it though, as the offer letter outlines very clearly where a new hire will sit in the organization and what their first week of work will look like. The have transformed the on-boarding process by starting with the offer letter vs. waiting for a new employee to sign and come on board. Perhaps this is an attempt at self fulfilling prophesy (if we tell them about their first week, they’re more likely to accept our offer!), but regardless, the effort to be transparent sets this company apart from so many of the humdrum companies doing the same old thing.

Just because it’s been done that way forever, doesn’t always mean it’s the best way to do business and it certainly won’t set you apart from your competitors. Many entrepreneurs are getting advice from old-school investors and advisors who saw it done a certain way that worked in their day, but that doesn’t mean that’s how it has to be done. If you choose to take a new approach, don’t do it for the sake of being different, do it because it either enables your company to run more efficiently and/or it adds value for your employees or customers.

Have you transformed your business beyond the new products and services you offer to your customers? Share what you’ve done in the comments.