Advice to Grads: Join A Winning Startup (v. 2017)

It’s that time of year again! Graduating students hungry to dive into the startup community (aka StartupLand) are eager to start their careers but struggle to select the right, specific opportunity. Each spring, I provide a comprehensive list of exciting, growing, hiring startups–both private or recently public–that are worthy of consideration as places to start or continue a career in StartupLand.

Before we get into the companies themselves, I suggest checking out my post Seeking a Job in Startup Land, where I give some advice on how to select the right company for you. Once you have reviewed this framework for deciding what you’re looking for, this post will give you a list of over 350 companies to research and approach.

As usual, the list is compiled and organized based on location since I believe in selecting a geography to plug in to (and contribute to) a community and ecosystem. I received fantastic input from angels, entrepreneurs, lawyers and VCs across the world, helping me pressure test and compile this list (note: Flybridge portfolio companies are in blue). I’m sure I made many mistakes and omissions, which are all my own. Feedback welcome!







ATL: Kabbage, MailChimp

CHI: AvantCredit, BucketFeet, Civis Analytics, Dough, Inc., Fooda, Groupon, Iris Mobile, Kapow, Narrative Sciences,, RemoteYear, ShopRunner, Shiftgig, SpotHero, SproutSocial, Uptake

CO:  FullContact, Ibotta, LogRhythm, Rally, SendGrid, Sympoz, TeamSnap, VictorOps, Webroot, Welltok

DC: 2U, Cvent, Optoro, Sonatype, Tracx, Vox Media, WeddingWire

SEA: Apptio, Avalara, Avvo, ExtraHop, Julep, Juno, Koru, Peach, Porch, Pro, Redfin

UT: Bamboo HR, Canopy Tax, Domo, Health Catalyst, Hirevue, InsideSales, Instructure, Lucid Software, Observe Point, Pluralsight, Qualtrics, Solution Reach, Workfront

That’s it! Edits/suggestions welcome. Special thanks to all those who provided me with input (who shall go nameless to protect the innocent) as well as my colleague, Nick Shanman.

How To Raise Your First Round of Capital

I gave a presentation this afternoon to my Harvard Business School class about how to raise your first round of capital. For those interested in seeing my advice on this topic as a former entrepreneur turned VC who has written a fair amount about fundraising, here are the slides:

I welcome any feedback or stories you might have!

Why “Ops” Is Taking Over Startup Land


A little over a year ago, I wrote that for startups, the Secret Weapon for Scaling was Sales Operations.

Since my writing about the importance and value of Sales Operations (where there are now 11K job openings on LinkedIn for this role), I have observed with great interest the explosion of operations functions in every function in Startup Land (a less geographically biased way of referring to the world of startups than “Silicon Valley”). Here are a few examples:

  • Business OperationsOne of my talented HBS students works for the finance department at Pinterest in a job titled “Business Operations”. I have seen many of my portfolio companies create this role under the CFO as a complement to FP&A (financial planning and analysis). Whereas the FP&A function is typically responsible for instrumenting the financial metrics and reporting them, the Business Ops function has emerged as the group that interprets the strategic implications of the business metrics more broadly and then formulates and drives new initiatives cross-functionally to address key issues. For example, how do you measure the success of a new product launch — and what do you do post-launch about the results you do measure? Business Ops focuses on decisions, not just data, and then helps operationalize those decisions within a startup. A quick LinkedIn search shows 15K openings for Business Operations, 15M title holders in the network, including companies like Circle, Lyft, NerdWallet and many others.
  • Product Operations: One of my portfolio companies, DataXu, recently created and filled the position head of “Product Operations”, a role that reports to the CTO who manages the entire 150+ product and engineering team. That executive will be responsible for measuring the product development process and implementing the necessary changes to make it more effective. They are also charged with training new hires and managing vendors. In short, they are like a “COO” or “VP of Ops” on behalf of the product organization. DataXu is not alone in hiring for this role. A quick LinkedIn search shows 6K opening for Product Operations and 200K title holders, with executives holding this title at growth stage companies like Fuze, Sonos, Wayfair and many others.
  • Marketing Operations: One of Flybridge’s marketing advisors has been discussing with me the rise of this role. The Marketing Ops role has been created because of all the data coming out of marketing automation tools and other systems. Marketing Ops makes sure that the right leads are being transitioned to sales in the right way and that the sales reps are using the sales force automation systems properly and that they are integrated with the marketing automation systems. Marketing Ops might be the group that scores the leads, tracks them through the sales process and does the win/loss post-mortem analysis. Watching the data, making sure it is integrated across the organization, managing the marketing systems, and reporting cross-functionally on key marketing metrics are all the jobs of the marketing ops function. Our portfolio company, MongoDB, has a nice job description for their open position — Director of Marketing Automation and Operations — that tells the story well. There are 5K openings on LinkedIn for this role and 9M people with that title in their profile.

Why has Startup Land suddenly gone bonkers over Ops roles and embedding them within every function? I think the simple answer is Big Data and process maturity. As companies stabilize their business models and find product-market fit, they begin to adjust from a hunch-driven operating model, where decisions are made by the founders in large part on gut instinct, to a metrics-driven model, where decisions are made by professional managers based on data. With the availability of so much data across all functions to professional managers, they need more analytical and operational horsepower to synthesize that data and derive insights from them that drive the business. Hence, the thirst for an operations staff—analytical, mid-level executives who can get into the weeds, derive insights and turns insights into action cross-functionally.

I have been preaching this message to all my portfolio companies: if you’re a startup executive and haven’t begun to operationalize your organization, you’re at risk of falling behind.

You Know What’s Cool? $1 Billion in Revenue…and Still Run by the Founder

Image result for 1 billion image

As 2016 comes to a close, one local company here in Boston is about to cross $1 billion in revenue: athenahealth. Going from zero to $1 billion in revenue is an extraordinary achievement, particularly for a company that is also very profitable (which athenahealth is).

Here is something even more extraordinary – the company is still run by its founder and CEO, Jonathan Bush. In fact, the number two executive in the company, COO Ed Park, is also a founder and is just now stepping down after nearly two decades running the company.

And here is something even more extraordinary still:  look around Boston, and you find that four of our emerging anchor companies have also just recently crossed $1 billion in revenue, are very profitable (except for Wayfair, who is free cash flow positive) and are still being run by their founders. Put this list on one chart, and it’s pretty remarkable:

Company Founder/CEO 2015 Revenue ($M) 2015 Adj EBITDA ($M) MarketCap ($B)
Akamai Tom Leighton 2,197 897 11.3
athenahealth Jonathan Bush 925 184 3.8
TripAdvisor Steve Kaufer 1,492 466 7.2
Wayfair Niraj Shah 2,250 -16 3.2

As 2016 comes to a close, it is worth celebrating the extraordinary achievement of these four tenacious and talented entrepreneurs. At a time when there is a lot of cynicism regarding unicorns and paper-based valuations in Startupland, it is refreshing to see four founders who not only took their company from zero to IPO, but continue to lead their companies to over $1 billion in revenue and beyond.

For more about the stories of three of these companies, you can see a few mini-case studies that I wrote a few years ago here:

Again, hats off to each of these four founder/CEOs. Their stories are definitely worth studying!

To Hack.Diversity, We Need to Come Together

Last January, I read a Bloomberg BusinessWeek cover story, Why Doesn’t Silicon Valley Hire Black Coders. I was struck by it because it went to the heart of an issue that has bothered me for years.

The innovation economy has two fundamental, related problems threatening its growth and sustainability: (1) a severe lack of technical talent, leading to a persistent hiring shortage; and (2) a severe lack of diversity, leading to a monolithic perspective.

For some reason, and despite generally good intentions, the demand for talent and the supply of diverse talent has not corrected itself naturally. My conclusion, after reading the article and talking to many experts in the area, is that tech’s diversity problem is a market failure due to a fragmented talent pool of diverse candidates, under-resourced recruiting functions at startups, cultural friction and social networks that don’t naturally overlap. This problem was one that needed an intentional, strategic solution.

Inspired to address this complicated issue, a group of private and public sector leaders in Boston has been meeting over the course of this year. Today, we are pleased to announce the launch of Hack.Diversity, an initiative to increase the breadth of talent into our innovation economy. The program will be managed by the New England Venture Capital Association, which seemed an appropriate place given its role as a hub in the innovation ecosystem (and Hack.Diversity is similar to the student internship program, TechGen).

Hack.Diversity is bridging the gap between Boston’s innovation economy and communities of color. The program will recruit, train, and mentor Black and Latino computer science and engineering graduates throughout Massachusetts, and create a pipeline of opportunity into the innovation economy, while also coaching our companies on diversity and inclusion. The goal is to address both the severe lack of diversity in the technical ranks of our top, innovation companies and help students of color find attractive career opportunities in technology. Our first talent partners are Bunker Hill Community College, Resilient Coders, UMass Boston, WPI and Year Up. Our first employer partners are Carbonite, DataXu, Hubspot and Vertex Pharmaceuticals. In addition, we are building a mentorship network of dozens of executives of color in the Boston tech sector to link up one on one with each intern to help coach their pathway to career success.

A few articles written about the initiative can be found here:

If you’re interested in being a part of the program — as a mentor, employer, donor or aspiring participant, check out the website:

If we can bring the two Bostons together to address the inequality and divisiveness in our community, we can create a shining example for others throughout the country.

Why Liberal Arts Majors Make Great Product Managers

There is a canard rampant in Startup Land that you need to have a computer science or engineering degree to be a great startup product manager. As a computer science major whose first job in tech was as a product manager, and as someone who has worked with (as both an entrepreneur and venture capitalist) and taught (as a professor at Harvard Business School) hundreds of product managers, I can tell you that this line of thinking is simply bull. And it may be leading to perpetuating the industry’s gender imbalance.

Let me explain by first focusing on what the product manager job requires.

What Is The Job?

An effective product manager is an entrepreneur, strategist, technical visionary, cross-functional team leader, and customer advocate all rolled into one. They try to understand what it means to walk in the shoes of the customer — what their problems are, what their environments are like, what they read, who they talk to, who they listen to, what their worries are in life. And then they try to extrapolate those insights into personas they can use as an anchor for product design decisions.

At a high level, product managers have three primary responsibilities:

1. Defining the product to be built — whether a new product or an evolution of an existing product — through a customer discovery process.

2. Negotiating and securing the resources to direct towards product development, or prioritizing the already allocated resources

3. Managing product development, launch, and ongoing improvement by leading a cross-functional team — the team members report directly to someone other than the PM, however, so while the PM has considerable responsibility, you might also have little formal authority over other staff members.

The product manager role is a general management position, so product managers tend to be generalists rather than functional specialists. Some of the best product managers are simply great communicators. They’re clear thinkers who have strong interpersonal skills and good judgment. It’s more about character and makeup and the broad skills you develop either in a professional or graduate environment, where you learn to be an effective communicator, a good writer, and a good interpersonal communicator. Where you learn to make decisions crisply. Where you learn to handle ambiguity.

Guess what? Those skills are all consistent with a liberal arts education. As Fareed Zakaria puts it in his book, In Defense of a Liberal Arts Education:

A liberal education teaches you how to write, how to speak your mind, and how to learn — immensely valuable tools no matter your profession. Technology and globalization are actually making these skills even more valuable as routine mechanical and even computing tasks can be done by machines or workers in low-wage countries. More than just a path to a career, a liberal education is an exercise in freedom.

Yes, it helps to be technically proficient, but for that, take an online class or two at our portfolio company, Codecademy. Great product managers need to know how to talk to engineering, but that’s communication not coding. They need to be effective in evaluating decisions and drawing on business judgment, but that’s analytical thinking not analytical programming.

A Few Profiles

Let me share a few profiles of amazing senior product leaders that I know by way of example:

  • Yasi Baiani, a senior product leader at Fitbit, the wearables leader that has a market capitalization of $3 billion. On the side, Yasi is about to embark on teaching entrepreneurship and product management at her alma mater, Berkeley. She majored in business.
  • Melody Koh is head of products at BlueApron, one of the hottest private companies in NYC, a revered unicorn, and rumored to preparing for a 2017 IPO. She studied commerce and economics at the University of Virginia before entering Startup Land.
  • Adam Medros is head of products at TripAdvisor, where he has been for over twelve years, helping lead them to a nearly $10 billion market capitalization. Adam’s major before joining Startup Land? Economics and German at Dartmouth.

Guess what each of these product leaders has in common? Spectacular communication skills, leadership ability, product passion and business judgment.

Why This Matters

In addition to making sure startups are open to hiring and training the very best, I am drawn to this topic because I think it results in a subtle barrier for women to become entrepreneurs and venture capitalists. The prevailing wisdom is that the best entrepreneurs are former product leaders. And there is a prevailing wisdom that former entrepreneurs make the venture capitalists. Therefore, if you accept the prevailing wisdom to be that only former coders can become great product leaders, you are limiting your entrepreneur and venture capital funnel to a narrow pool of candidates, with 88% of engineers being men. That’s bad policy on many, many dimensions.

But I am passionate about this topic for another reason. I love the product management function — it is where I started my own career — and want to see the discipline be an excellent opportunity for everyone. That is why I continue to teach about it, write about it and talk to my portfolio companies about it.

So stop telling folks they need to be former engineers or computer science graduates to become product managers. Hell, hire a Symbolic Systems major and watch what magic can happen.

A VC Perspective on AngelList


I have long been a fan of AngelList, an innovative online platform for startup funding and recruiting. I have watched the rise of the platform with great interest and enjoyed playing with it around the edges.

Over the last few years, individual angels and even some firms have used AngelList to create investment clubs to invest in individual startups in what are known as syndicates. More recently, funds have used AngelList to create special purposes vehicles (SPVs) for follow-on investments in portfolio companies.

My Flybridge partners and I decided we would try a new twist on the model by creating a small fund on AngelList as a platform to make seed investments centered around a particular community and theme. To that end, a few months ago, we created something we call The Graduate Syndicate fund, a $2.4 million seed fund. BostInno wrote a bit about it here.

The Graduate Syndicate will invest $100,000 in compelling startups founded by recent Harvard graduates, particularly out of Harvard Business School (HBS). As a faculty member in the Entrepreneurship Department over the last six years, I have had the opportunity to teach hundreds of brilliant, enterprising students. Flybridge has invested in a few of them, but many of the recent graduates (and only graduates, in compliance with Harvard’s conflict of interest policy) are at such an early stage — pre-seed or seed — that they are pre-institutional at the time that I am advising them. As with our other investments, our goal is to back outstanding entrepreneurs who are pursuing large, disruptive opportunities that we think can generate outstanding returns. But by operating more like an angel — we don’t price the deals or take board seats, we don’t require partner meetings but instead make decisions after a few meetings given we already know these entrepreneurs well — we can be more flexible with regard to process, stage, sector and geography.

The other thing we decided to do in creating the fund is to invite some of our friends to invest alongside us who are from the Harvard community. So, in addition to Flybridge IV (our fourth fund, which we are currently investing out of), the LPs in The Graduate Syndicate are a handful of HBS professors and alumni who are excited to support the young entrepreneurs, many of whom they had in their classes or have been advising as Entrepreneurs in Residence (EIRs). We also assembled a group of recent alumni entrepreneurs as advisors to be available to coach the founders through the ups and downs, particularly in the early years before they have more formal advisors or boards.

The benefits of The Graduate Syndicate to entrepreneurs are compelling: pre-seed money from a trusted advisor, a network of amazing LPs and experienced entrepreneurs available to them, and inclusion in the broader Flybridge network of nearly 100 portfolio companies. Since creating The Graduate Syndicate a few months ago, we have made eight investments:  Amartha, Baroo, Camino Financial, Digital Outposts, Fitzroy Toys, Funding Societies, Getaway and Robin Health. The website lists them all, but the plan is to run the experiment for the next year or two and then assess the results.

Having created this new model on AngelList, I thought I would share a few observations as a venture capitalist working with the platform:

  1. Smooth Back Office. Although we have our own, crack finance team, when you are investing on AngelList, you are benefiting from a very experienced back office team, with existing contracts and processes. Collecting and tracking numerous small dollar investors has an overhead attached to it. The AngelList team has been absolutely first rate to work with.
  2. Brand/Reputation. Like many leading platforms, there is a brand and reputation benefit to working with AngelList. LPs who knew it (although many did not) were immediately comfortable with jumping on the platform and investing through it. Similarly, the startups we have invested in are all listed on AngelList and were comfortable with the flow of agreements and money. Over time, I would expect more investors to jump on the platform, making it even easier to work with.
  3. Capital. In theory, AngelList also brings capital. We haven’t utilized this feature for The Graduate Syndicate because we are a closed fund (that is, for the first fund, we only allowed LPs who we knew well and trusted to participate). But for our startups, we expect to see funds like CSC (who committed $400m to AngelList companies last year) and others become sources of available capital.
  4. Work in Process. We were breaking new ground with AngelList and the team has been outstanding in working through the issues, but there are still some rough edges. For example, although we don’t charge any fees for The Graduate Syndicate, there needs to be a fee mechanism in place before other funds will jump on to the platform. AngelList is working on adding this feature and many others.

All in all, creating a fund on AngelList has been a very positive experience. If anyone would like to learn more from our experience, let me know!