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!

The Three P’s: Lenses to Assess Your Startup’s Performance

I took a bit of a sabbatical this summer and now, refreshed and with a few new topics brewing, it’s time to get back to writing!

LunettesA recurring theme I’ve encountered this summer is which lenses you should apply when evaluating the performance of your growing organization. As an advisor and executive coach to early stage companies, I’m finding more often I am preaching the concept of the “Three P’s: People, Processes and Programs”. Looking at your company or department through each of these lenses and asking yourself how you’re doing in each area can be very telling. It helps you understand where you may need to improve to continue to scale and reach success.

Lens #1 – People

The best leaders of any organization know that their people are what makes or breaks the success of their company. This isn’t just about performance and productivity metrics of each member or as a team, this is about people being in the right roles, having the right training, career path and great peers, bosses and teams to work with. When you ask yourself “are my employees happy?”, consider if you are doing everything you can to ensure greatness. This is well beyond great pay and company perks or weekly beer bashes. Most people want to feel challenged in their roles, but also supported and set up for success. They want equally smart (or often smarter) people to work with and they want to see you get rid of people who don’t work as hard as they do or who are jerks.

Great employees want to work towards growth either as an individual contributor or as a leader. They want to know that they will be rewarded for making solid contributions and for being team players. Growth should not always come from taking on more responsibility or more people to manage. Growth can also come from broadening their knowledge through exposure to new things such as customer visits, interactions with your board, or maybe going to a conference or speaking on a panel with other domain experts. When an employee is not growing or rising to a new challenge, ask yourself if this is a limitation of the individual, or is the system limiting them? Do they need mentorship from someone who’s been in their shoes before to guide them to the next level? Are you micromanaging, thus not giving them a chance to step up and show what they can do?

Happy employees also feel like they have visibility into the vision and direction of the company. They don’t need to know every detail of a product roadmap or the revenue strategy, but they want to understand where the company is headed and how leaders of the organization are measuring success. As a leader of an organization, do you have weekly or monthly all-hands and/or quarterly reviews that include vision and strategy? Do you routinely communicate through company email or on-line forums (e.g., Slack) on big company news like closing a big deal or a great new hire and include why these are important? The more understanding each employee has about the big picture, the more they can calibrate their actions and contribute towards success.

This first lens – evaluating if you are setting up an environment for happy, growing and informed employees – is probably the most important thing you can do to set your company up for long term success.

Lens #2 – Processes

As much as any startup loves being small, nimble and usually pretty organizationally flat, the reality is that implementing processes can be useful. I’m not talking about three ring binders full of protocols and standards. I’m just saying that having a general process for key parts of the business is important. There was probably a time (or maybe your company is there now) where everyone sat around one table and could just talk through how to get something done. Then, all of a sudden, one table becomes a few desks, maybe a few remote employees and a field sales person or two and what used to be a simple chat becomes harder to navigate.

ProcessConsider what processes are in place today that grew organically vs. with intention. If the organic processes work, that’s cool, but keep an eye on them because over time they may not scale. For those set up with intention – e.g., a hiring process or maybe your weekly sprints – reevaluate them on a regular basis. Are they repeatable and do they scale with more people in the company or more bugs to fix? Resist the temptation to keep a process because “that’s how we’ve always done it” or because “our Founder set it up, so how can we kill it?”. Companies that evolve have processes that evolve and what once worked then, may not work now.

Think about how decisions are made, information is disseminated and loops are closed for critical processes first. The most common areas where processes comes more and more into play tend to be product roadmap and execution plans, hiring strategies and go to market strategies. Here are some suggestions for each:

Product Roadmaps

  • Consider monthly, three-months-out roadmap reviews to prioritize new products, major features and release plans. Do not lose sight of the fact that this is not just which designers or engineers are building what, but also how you’ll market and support these products and features.
  • You may have weekly reviews to ensure you’re tracking to the meta-plan and make adjustments if needed. Have some sort of process in place to deal with surprises like a critical bug that bumps a feature or a customer opportunity that may change the priority of a future feature. Set criteria that justifies this type of change so you don’t have to analyze each one on the fly. For a critical bug to bump a priority feature, it might be something like “must impact >50% of our customers or degrade performance more than “20%”. For a customer opportunity it could be “must be a deal worth >$(?) revenue or a customer that will provide undeniable street cred for >50% of our current prospects”.
  • If/when the roadmap changes, have a process for letting people know. Don’t just update Trello and assume everyone will see it – have some sort of change management message that goes out via email/slack that tells the team what and why.
  • It also doesn’t hurt to have a process to track changes to the roadmap so you can see the impact on your initial plan over time. This will contribute to better planning going forward.

Hiring

  • I highly recommend a quarterly hiring plan – not just how many new heads, but actual roles you intend to fill. Given today’s climate where hiring is SO hard, it could take 2-3 months to get that right candidate. So have a process in place to assess where you are with hiring and what new roles you need to ramp on filling.
  • Get in the habit of a regular job description (JD) writing process. Don’t always wait for a role to open up. If people are in the role now, have them write their own job descriptions. This not only helps when it comes to review or promotion time, but you then have these JDs on file if/when needed. I’ve seen major delays with filling a pipeline with good candidates or terribly inefficient candidate interviews simply because no JD exists.
  • Have a hiring process in place that starts with the JD and ends with the on-boarding of this new hire. I’ll write a future post on this with more details, but the short story is that it should include how you’ll post and market the opening, handle phone screens, on-site interviews, making an offer, negotiating terms and how you’ll get that new hire on board and productive as fast as possible.

Go to Market

  • It’s one thing to have a product roadmap that outlines what you’ll build, but it’s another to say how you’ll get those things out there. With every product roadmap, there should be a parallel process for laying out how and when new products/features are publicized, priced (if applicable) and sold.
  • Have a process for content updates such as your website, marketing materials, and demos.
  • What process will you have for telling the world about your new stuff? Do you have a regular list of press or industry bloggers who write about your company or trends in your market? When should they hear about your new product/feature and what’s your plan to share what they write through social media or other channels?  How do your current customers and/or prospects hear about the latest new thing? These are not afterthoughts once the engineering is done, they are just as important processes to get in place as your code check-ins and testing procedures (which you have already, right?).

Looking through the lens of processes and seeing what you have and don’t have in place should tell you whether your company will be able to scale or is heading for a train wreck. Don’t be afraid to pause when you see a gap where a light process could relieve a bottle neck or better prepare your team for future scaling challenges.

Lens #3 – Programs

The Program lens is not used as often as it should. Granted, as a former Program Manager in a past life, I’m a little biased. However, what I often see missing in growing organizations is someone looking across the organization, programmatically, to ensure all the pieces are coming together including people, schedules and money.

A great example of this is the processes I mentioned above around new products or major feature releases. These are often multi-pronged activities involving engineering, sales, support, marketing and maybe finance and operations. You may have program_managerheads of each of these groups, but who is overseeing how they all work towards a common goal or launch date? For many small companies, that’s the CEO or CPO, but (oh by the way), these same people are running your company or out in the field selling or closing your next round of funding.

In the early stage, you may consider rotating the role of Program Manager between different leaders in your organization. Keep in mind, though, not everyone has the knack for project plans and cross-company communication. Make sure you pick the right people to be in this role.  As your organization grows, consider hiring an actual Program Manager. A Program Manager is often one of the unsung heroes of a company because they are in the background instead of on the front lines. They quietly prod and check things off lists. They communicate what’s happening and where there are possible gotchas. Program Managers beat the drum so everyone is marching in the right direction and at the right pace. They are masters in GSD (Getting Sh-t Done) with no task too small or ask too big.

So, don’t just look through the process lens, but also ask yourself what programs are cutting across more than one part of your company and who is orchestrating them. You’d be amazed how productive and efficient your startup will be when programs are well managed.

In Summary….

Startups, when they’re working, develop very quickly – often without enough attention given to people, processes and programs. It’s one thing for an Advisor or Investor to tell you what your company or department is lacking or how you could be doing better, but in the end, you need to ask yourself how YOU think it’s going. Applying these three lenses should help bring things into focus [pun intended].

Have you been using any of these lenses to assess performance or have different lenses that you’ve found effective?  Please share in the comments below!

A Startup’s Guide To Having A Great Summer Internship Program

So, you’ve decided to hire some interns this summer. Well done! Often, early stage companies shy away from hiring summer interns because they dread the idea of “babysitting” on top of everything else that needs to get done. If you’re bringing one or several interns on, you know it is well worth the effort because interns:

  • are potential future full-time hires;
  • can work on stuff no one has time to do, but would be great to have (often referred to as “gravy projects”); and
  • they are walking advertisements of your company and your product(s).

Whether your company is fully established or just getting started, having a well thought out program for your interns will ensure that you get the most out of them and that they get the most from their experience at your company. A great experience means they’ll be talking up your company and your product(s) when they head back to school. Thus, they will be walking advertisements for future hires and future customers.

A Guide to a Great Internship Program

Let’s assume you’ve already made great hiring decisions for the summer and students are coming to work for you for approximately 10 weeks. I’m not going to get into salaries, temporary housing, or other pre-hire logistics in this post, but I will walk you through an outline for a solid internship program. It’s geared towards engineering types of interns, but most applies to any intern role.

The Timeline

  • If you have more than one intern coming on board this summer, try to have them start around or on the same date. This eases the burden of on-boarding processes by orienting everyone as a group and gives them a sense of belonging to a cohort from the get-go.
  • After orienting them to the office and getting them all the necessary logins, etc., do a kick-off lunch with founders and mentors to welcome them to your company.
  • Outline a weekly schedule for the intern program. Many interns have not worked in a business setting before and will need structure with a clear beginning, middle and end to their program. As much as they’ll appreciate a clear understanding of their summer schedule, this should also help your team balance their time around intern commitments. A sample schedule is below (click on the image for a larger view).

Sample Internship  Program ScheduleMentors

  • Every intern should be assigned a mentor. This is not typically their hiring manager, but rather a peer or someone slightly senior to them who can guide them through project specifics (e.g., coding standards or pricing models) and help them assimilate to the company culture or maybe even to a new town if they’ve temporarily relocated for this job.
  • Mentors should be briefed on HOW to be mentors. Make sure they understand the difference between being a guide and being a boss. No one wants two people telling them what to do all the time. Also make sure you pick someone who wants to be a mentor – this is a great growth opportunity for your team, but if they’re not up for it, it could make for a suboptimal experience for your intern.
  • Mentors should be generally available over the summer for ad hoc questions as well as weekly 1:1s. If someone is taking more than 2 weeks off this summer, they should not be a mentor.
  • While it’s nice to do, a mentor does not have to be a domain expert for the intern’s summer project. As long as they know how to help the intern get access to the experts and can guide in other ways, they are qualified!
  • Mentors should be expected to give feedback to their intern’s manager on performance and possible offers to return to your company for another summer or full time role. Mentors should not make such offers themselves. This is the intern’s manager’s role!

The Project

  • It’s good practice for companies to keep a running list of possible intern projects throughout the year. Again, gravy projects are ideal – meaningful and useful projects, but if they are not completed, it does not put your company at risk.
  • Try to offer projects to your interns that will:
    1. Allow them to stretch beyond their comfort zone.
    2. Result in something tangible that others will use such as code that ships, content on a public website or even a tool that helps an internal team be more productive. Ideally, it has a result that can be listed as an accomplishment on their resume and added (or strengthened) a skill.
    3. Encourages them to get to know your company/products (remember, walking advertisements). For example, one that lets them dig into customer data or one that requires them to work with people from other parts of the company such as sales or support.
  • There are two different approaches I like to assigning intern projects. Either have a list of projects to offer when they start and let them ask questions and explore them a bit in the first week, then they pick one. Or, in advance of their start date, ask them questions about what skills they’d like to develop this summer and before they start, you and their mentor can pick the one best suited for their skills and goals.
  • Try to offer one or two meaty projects at most for the whole summer vs. several small projects that could limit their learning experience.
  • Pre-reads: Whether you have a project in mind before they start or a list of possible projects for when they start, it’s nice to send a suggested reading list and some company info to your hired interns a month or so before they start. Don’t overdo it since they are probably cramming to finish the semester. Just send things that will give them a leg up. Even with an NDA they still may be a bit clueless about what not to share, so don’t send them secret sauce information!

Learning and Having FUN

  • Interns chose to be interns instead of scooping ice cream this summer because they want to learn. Invest in them and expect that they want to understand as much as they can about how everything works at your company.Lunch-n-learn
  • Beyond what interns learn doing their project, consider offering weekly lunch-n-learn sessions where food is brought in (or they get their own if your company is being careful about burn!) and have someone do a talk. Change it up and do everything from a technical talk to a business talk to maybe inviting a guest speaker like one of your company advisors or a customer or partner. Also, talks should be relevant and understandable whether you’re a coder or a marketing intern.
  • Look for opportunities for interns to have a unique experience. For example, tagging along on a customer visit or helping out in the company booth at a sales conference. Not only is it nice to have an extra set of hands, but interns will be SO appreciative for these extra opportunity to get different perspectives of your business.
  • Include interns in routine company meetings and off-sites. They are employees of your company and these are also learning experiences.
  • Make time for fun. Take them bowling or a baseball game. If your interns are new to the area, show them the city via a Duck tour. Mentors should come along as well as part of the bonding process. The summer at your company should be memorable for interns beyond the work they did.
  • If your company is based in MA, enroll in TechGen, a program from the NEVCA, which has lots of professional development and social resources for your interns and is also a great place to source talent.

Wrapping Up

  • Throughout the summer, you should schedule time to give your intern feedback on their performance and for them to let you know how they think they’re doing. In addition to weekly 1:1s with their mentor, there should be a mid-summer review and end of summer exit interview. You don’t want to find out at the end of the summer that your intern had a horrible experience! They’re at a startup, so things will undoubtably change unexpectedly. Course correct throughout the summer as needed and help them understand that this is the nature of early stage companies.
  • In preparation for the mid-summer review, ask mentors to feedback to managers how interns are doing. Factor this into a potential decision to re-hire interns for the following summer or offer a full time job for when they graduate. Interns should be told that this is a possibility OR NOT. Do not set false expectations. If your company cannot commit, then make it clear that good interns will be the first people you’ll call when you are hiring.
  • The last week of the internship should be for closing things out. Checking final code in, writing documentation and/or tests, doing a code-walk for whomever will take over when they go, and maybe doing a demo day or poster session so interns can see each other’s work. Also, plan for one last fun outing so people can say goodbyes and feel all warm and fuzzy about their experience. Schedule this last event when most/all of your interns are still around. Even if a student is returning to a nearby campus, it’s not reasonable to expect them to come back to work even if it is for something fun.
  • If you are offering a sign-on bonus for a full time position when they graduate, give 50% of it in their last paycheck with no strings and hold the other 50% for them if they are to return. The second half will be in their first, full-time, paycheck. Start to finalize your plan to offer or not around two weeks before the intern leaves.
  • If your intern(s) are returning to local schools, consider offering them part-time work during school (with potential for full time during breaks). It’s a great way to maintain the relationship and further lock them into a future full time position.

Your company does not have to be big and profitable to be thoughtful about the internship experience. In fact, starting when you’re small and nimble will ensure that a strong internship program is part of the fabric of your company as you grow. Just envision smiling interns back at school raving to their friends about their best summer ever and the returning faces and quality resumes you’ll see next hiring season!

Have you worked (or currently work) for a company with a great internship program?  Share tips and tricks that made it great by replying with a comment.