Go Big, Or Go…Startup

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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!

So You Want to Be A Product Manager

Because I teach a course on Product Management at Harvard Business School, I am routinely asked “what is the role of a Product Manager?”. The role of a Product Manager (PM) is often referred to as the “CEO of the Product”. I disagree because, as Martin Eriksson points out, “Product managers simply don’t have any direct authority over most of the things needed to make their products successful – from user and data research through design and development to marketing, sales, and support”. PMs are not the CEO of product and their roles vary widely depending on a number of factors. So what should you consider if you’re thinking of pursuing a PM role?

As an aspiring PM, there are three primary considerations when evaluating the role: Core Competencies, Emotional Intelligence (EQ) and Company Fit. The best PMs I have worked with have mastered the core competencies, have a high EQ and work for the right company for them. Beyond shipping new features on a regular cadence and keeping the peace between engineering and the des

ign team, the best PMs create products with strong user adoption that have exponential revenue growth and perhaps even disrupt an industry.

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Do you have what it takes to be the best PM?

Core Competencies
There are core competencies that every PM must have – many of which can start in the classroom – but most are developed with experience and good role models/mentoring. Some examples of these competencies include:

  • Conducting customer interviews and user testing
  • Running design sprints
  • Feature prioritization and roadmap planning
  • The art of resource allocation (it is not a science!)
  • Performing market assessments
  • Translating business-to-technical requirements, and vice versa
  • Pricing and revenue modeling
  • Defining and tracking success metrics

These core competencies are the baseline for any PM and the best PMs hone these skills over years of defining, shipping and iterating on products. These PMs excel at reflecting on where each of these competencies contributed to the success or failure of their products and continuously adjust their approach based on customer feedback.

Emotional Intelligence (EQ)
A good PM may know the Do’s and Don’ts of a customer interview, but the best PM has the ability to empathize with customers in that interview, are tuned into their body language and emotions and can astutely suss out the true pain-points that their product/feature will address. A PM with a high EQ has strong relationships within their organization and they have a keen sense of how to navigate both internal and external hurdles to ship a great product. Here’s a deeper look at how the four EQ key traits, as defined by Daniel Goleman, relate to the PM role:

  • Relationship Management: Probably one of the most important characteristics of a great PM is their relationship management skills. By forming authentic and trustworthy connections with both internal and external stakeholders, the best PMs inspire people and help them reach their full potential. Relationship management is also vital in successful negotiation, resolving conflicts and working with others toward a shared goal which is especially challenging when a PM is tasked with balancing the needs of customers, resource constrained engineering teams and the company’s revenue goals.

    Authentic and trusting relationships within an organization can lead to more support if additional funding is needed for a product or to sway an engineer to include a quick bug fix in the next sprint. Outside an organization, these skills could encourage existing customers to beta test a new feature for early feedback or convince a target customer to try the MVP of a product still in stealth mode. These relationship skills can also be what makes the difference between having irate customers because of a bug introduced into the product and those who say “no worries, we know you’ll fix this!”. 
  • Self-awareness: PMs must be self-aware to remain objective and avoid projecting their own preferences onto users of their products. If a PM is in love with a feature because it addresses their own pain points (PMs are often super users of the products for which they are responsible), they may cause a user to say they love it too just to please the PM (“False positive feature validation”). If not self aware, a PM may push to prioritize a feature they conceived even when all the customer interviews and evidence is stacked against it. This lack of self awareness could derail more important priorities and/or damage the PM’s relationship with engineers who may lose confidence in their PM when the feature isn’t readily adopted by users. 
  • Self-management: Being a PM can be incredibly stressful! The CEO wants one thing, the engineering team another, and customers have their own opinions about feature priorities. Managing tight deadlines, revenue targets, market demands, prioritization conflicts and resource constraints all at once is not for the faint of heart. If a PM cannot maintain their emotions and keep it cool under pressure, they can quickly lose the confidence of all their constituents. The best PMs know how to push hard on the right priorities, with urgency, but without conveying a sense of panic or stress. These PMs also know when to take a breath and step away if needed, regroup, and go back into the game to get sh*t done (GSD). 
  • Social Awareness: According to Goleman, the competencies associated with being socially aware are Empathy, Organizational Awareness, and Service. PMs must understand customers emotions and concerns about their product as much as they understand the concerns of the sales team on how to sell that product (or support team to support it, or engineering to build it). PMs have to have a deep understanding of how the organization operates and build social capital to influence the success of their product – from obtaining budget and staffing to securing a top engineer to work on their product. Finally, social awareness ensures the best PMs service their customers with a product that addresses their jobs to be done which is ultimately what drives product market fit.

Read more about what Paul Jackson has to say about EQ and PMs here – including a sub-link of an interview with Sam Lessin, former VP of Product Management at Facebook, who says he has ‘never successfully trained empathy.’ (or as Lady Gaga would say “you were born this way”…or not!)

Company Fit
So if the best PMs have well developed core competencies and a high EQ, does that mean that they are then destined for success no matter where they work? Going deeper, it is taking these skills and personality traits and applying them to the right company – amid a broad array of opportunities – that will ultimately guarantee success.

I have yet to see a standard job description for a Product Manager because each role is ultimately defined by the size, type of product, stage, industry and even culture of the company. Assuming the core competencies and high EQ as the minimum requirements, the next step is to unpack who’s hiring and what they are truly looking for:

  • Technical Skill – The type of product, who uses it and/or the type of company (e.g. Google who requires PMs pass a technical skills test regardless of what product they’ll work on) will determine how technical a PM needs to be. If the company is building a SaaS CRM, there may be more requirements for experience with go-to-market and customer lifecycles than how the product itself is built. If it’s a data science product with machine learning algorithms and APIs, the role may require a lot more technical depth to not only understand how to build the product but also how to talk, credibly, with the customers who will use it. That said, having a basic technical understanding of what is “under the hood” and mastery of the tools that PMs use is definitely important for the role, anywhere. Colin Lernell has more to say about these necessary skills here.

    If you are an aspiring PM concerned you lack the basic tech skills for the role, you might consider taking online courses such as the renowned Introduction to Computer Science (CS50) course offered by Harvard University or one of the many intro and advanced technology courses offered by The Flatiron School. 
  • Company philosophy about PM – Every company has a different philosophy about the product development process and where PMs fit into that process. Below are the three most common types with pros and cons:

    • PM Drives Engineering: A “throw it over the wall” approach where PMs gather requirements, write the quintessential PRD (Product Requirements Document) and hand it off to Engineering to spec out the technical requirements. Contemporary organizations may do this process in a more agile and collaborative way, but the expectation is that PMs know best about what customers need and engineering is there to serve.
      • Pro: Engineering can focus on coding without a lot of distraction; tends to work well for Waterfall development shops with long lifecycles.
      • Con: Engineers lose sight of the big picture and do not develop empathy for customers which can lead to a poor user experience; often there are unhealthy tensions when tech-debt and “plumbing” work needs to be prioritized against customer requirements. 
    • Engineering Drives Product: More technically oriented product companies (e.g., cloud, big data, networking…) tend to be engineering driven where engineers are advancing the science in their domain and PMs validate solutions or create front end access points (UIs, APIs) to tap into this new technology. There can be a collaborative relationship and feedback loop between customers, PM and engineering, but typically, PMs are serving engineering in these companies.
      • Pro: Breakthrough technology can offer customers things they didn’t even know they needed (VMotion at VMware was a great example of this. An engineer thought it would be cool to do, a PM figured out how to monetize it and it became THE billion dollar game changer for the company).
      • Cons: Engineers chase the shiny new thing, over-architect the solution or iterate forever (seeking perfection) before getting customer feedback; PM input on priorities are ignored, which is sometimes the most basic needs of customers to encourage adoption and increase stickiness of the product.

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    • The PM<>Engineering Partnership: There is a strong yin-yang between PM and Engineering where there is joint discovery, decision-making and shared accountability. Engineers join PMs in customer interviews and PMs are insprint meetings to help unblock tasks or bring clarity to  requirements, but the two roles respect the line where one starts and the other stops. PMs understand what’s being coded, but don’t tell engineers how to code and engineers have empathy for customers’ needs, but leave the prioritization to the PMs.
      • Pros: Streamlined prioritization process that values tech-debt/plumbing projects; better design processes leading to a more positive user experience; higher performing teams with improved product velocity, quality and typically, happier customers.
      • Con: Breakthrough innovation may not get light/investment; time-to-market may seem to lag (but I’d argue what’s released is far better aligned with customer needs with a far more scalable product).

I’m clearly biased (as is Fred Wilson) on the third type of philosophy about PM as I’ve experienced all three and found the yin-yang to be most effective, but it’s not to say the others are notably bad and, again, it really depends on what type of product, stage, etc,. Regardless, when considering a PM role, the philosophy of PM at the company could be the deciding factor on fit for the role.

  • Stage of company – The role of the PM at a startup is far likely to be responsible for “all the things” vs. a mature company where their role will be more distinctly defined. Eriksson, Banfield and Walkingshaw’s book Product Leadership has a section that has a lot more detail on this topic).

    • Startup: Beyond discovery, definition and shipping, they may also be responsible for pricing, marketing, support and potentially even sales of the product. These PMs thrive in a scrappy environment and are comfortable with ambiguity and frequent changes to direction as the company works towards product market fit and learns to operate at scale.
      • Pros: Likely to be more involved with company strategy, exposure to senior leadership/board, able to take more risks/make a bigger impact; more influence/authority over company resources.
      • Cons: Little-to-no mentorship or role models or best practice within the company (may have to seek externally); may not have requisite experience for some of the “things” (comfortable winging it); tight budgets. 
    • Mature Company: The PM may have a more narrow scope (deep vs. broad), have co-workers who handle pricing, go to market strategies, etc.. and likely part of a larger team of Product Managers.
      • Pros: More likely to have mentoring/role models and development standards/best practice; close association with an engineering team can develop strong relationships over time (great for long term impact/career growth); if product has market fit, there is an established customer base and performance baseline to work from vs. guessing until you get it right.
      • Cons: Less exposure to company strategy; just one of many voices of the customer; can get “lost” in the system; more politics; tight budgets. 
  • Founder/CTO/CEO relationship with PM – Especially in earlier stage companies, it’s important to know how involved the Founder/CEO/CTO is in the product process. If they are deeply involved, the PM role may play more of a support role to flesh out their ideas or validate concepts with customers vs. conceiving and driving ideas of their own. This can be great fun for some PMs who enjoy partnering with founders/c-levels and collaborate on the product evolution, but for some PMs it can be very frustrating if they prefer to take more ownership of product direction. It can also be challenging if the more technical founders/c-levels prefer working directly with engineers. This can leave PMs out of the loop or undermined (even if unintentional) causing not just personal frustrations but delays if they have to play catch up and/or continuously recalibrate. When considering a PM role that may work closely with the founding leadership team, be sure to find out their expectations of the PM function and decide whether this is the right fit with your interests.

There are of course many other factors to consider for any role such as the type of product you are building (B2B, B2C, industry, etc.), the humans with whom you’ll work and the overall company culture (diverse, inclusive, flexible work hours, remote culture, etc.), and of course compensation and benefits. There are also a million articles on hiring product managers to get perspective on what the hiring managers are looking for – I especially recommend my friend Ken Norton’s piece How to Hire a Product Manager. However, if you are striving to be the best Product Manager, consider all of the above before signing on to your next gig. Developing core competencies will be an ongoing activity throughout your career and leveraging a high EQ will ensure a more positive experience, but where you work, how they work and who you work with/for will ultimately determine your long term success.

Have additional pointers on succeeding in the PM role? Please share in the comments!