I was in a Board meeting last week (not Return Path’s), when one of my fellow directors came out with this gem:  “No one will ever thank us for keeping our prices low.”

When I first heard this, as is the case with most great quotes, I was drawn to its wit and simplicity.

But then I started thinking – is it true?  My mind first went to retail.  Having a reputation as being a low-cost provider can be in and of itself effective marketing – if that reputation is strong enough and your selection is wide enough, at least in retail-oriented industries, customers may consistently buy from you even if you’re not ALWAYS the low-cost provider.  Wal-Mart and Amazon prove this one out every day.  That’s the economic equivalent of customers thanking you for keeping your prices low.  Or pick an even more extreme example – gas stations, where there’s even more limited brand loyalty and even more product commoditization.  There’s really no reason to buy gas from a station who charges more than a couple pennies more per gallon than its neighbor.  No, thank you.

But in a B2B environment with smaller numbers of customers and smaller numbers of SKUs, this comment makes a lot more sense.  IT or Marketing departments don’t exactly go to the grocery store twice a week to buy data or software solutions!  I’m a big believer in the diminishing differences between the B2C and B2B universes, but this area may be one where the difference is still sharp.

Low prices might lure prospects to your doorstep, but they’re not going to keep buying your product if it’s not of sufficiently high quality.  Buyers measure quality in different ways, but here are three frameworks to think about as you contemplate the quality of your solutions relative to their prices:

• Is the quality of your product “above the bar”? Meaning, does it work well enough to get the job done that customers are hiring you to do?  If not, you do not have a sustainable business.  If so, see the next two questions
• Is the value of your product strong enough relative to the price you charge? Value-based pricing is increasingly difficult in an era of hyper competition, but if you can offer tailored enough solutions by vertical or of course by client, you can really optimize your pricing model
• Is your price/value equation strong enough relative to the price/value equation of a competing solution? Sometimes a “just barely good enough” solution can beat out a superior solution as long as it’s a LOT cheaper and the job the client needs done isn’t mission critical

The final thought vector in this equation is friction.  Go back to the consumer examples above – your switching cost to buy gas at Station A one week and Station B the next week is zero.  But in a B2B environment, there’s always at least some friction around switching products.  Friction could be implementation cost, time, execution risk.  It could be employee or customer training.  It could be integration with other systems or workflows.  It could even be desire to maintain a halo effect from doing business with you.  The more friction you have with your product, the easier it is to maintain higher pricing.

So my conclusion is that high prices are rarely going to chase someone away in a B2B, low client count/low SKU/moderate friction environment.  And that means my fellow director was spot-on:  no one will ever thank you for keeping your prices low.  All in, this comment was a great reminder for any B2B organization about how to think strategically about pricing.

(This is an excerpt from Chapter 23 of Startup CEO, “Collecting Data,” in which I write about the importance of observing and learning from customers and friends of the firm, as well as employees.)

Here’s a story for you that happened 10+ years ago. I’m sitting at the bar of Sam Snead’s Tavern in Port St. Lucie, Florida, having dinner solo while I wait for my friend Karl to arrive. I ask the bartender where he’s from, since he has an accent. Nice conversation about how life is rough in Belfast and thank goodness for the American dream. I ask him what to order for dinner and tell him a couple of menu items I’m contemplating. He says, “I don’t know why they don’t listen to me. I keep telling them that all the people here say that the nachos aren’t good because they don’t have enough beef in them.”

I order something else.

Five minutes later, someone else pounds his hand on the bar and barks out, “Give me a Heineken and a plate of nachos.”

The bartender enters the order into the point-of-sale system.

What’s the lesson? Listen to your front-line employees—in fact, make them your customer research team. I have seen and heard this time and again. Employees deal with unhappy customers, then roll their eyes, knowing full well about all the problems the customers are encountering and also believing that management either knows already or doesn’t care. There’s no reason for this! At a minimum, you should always listen to your customer-facing employees, internalize the feedback and act on it. They hear and see it all. Next best prize: ask them questions. Better yet: get them to actively solicit customer feedback

Thanks to my friend and long-time former Board member Jeff Epstein, I recently downed a new book, You’re in Charge – Now What?, by Thomas Neff and James Citrin.  I’m glad I read it.  But it was one of those business books that probably should have just been a Harvard Business Review article.  It’s best skimmed, with helpful short summaries at the end of every chapter that you could blow through quickly instead of hanging on every word. 

The authors’ 8-step plan is laid out as:

1. Prepare yourself during the countdown
2. Align expectations
3. Shape your management team
4. Craft your strategic agenda
5. Start transforming culture
6. Manage your board/boss
7. Communicate
8. Avoid common pitfalls

Ok fine, those make sense on the surface. Here are three things that really stood out for me from the book:

First, “working” before you’re officially working – the countdown period. I tried hard NOT to do this when I was between things, but I’m glad I did the things I did, and now, I wish I had done more. The most poignant phrase in the book is “scarce time available during your first hundred days.” That is an understatement. As my “to read” pile grows and grows and grows with no end in sight…I wish I had done more pre-work.

Second, remember that in every interaction, you are being evaluated as much as you are evaluating. And note that for many people, they will be thinking very critically, things like “do I want to work with this person…is he/she showing signs that he/she wants to work with me?” Yes, we all know as leaders, we live in a fishbowl. But I think that may be even more true during the first couple months on the job.

Finally, this phrase stood out for me: “Acknowledging and in some cases embracing your predecessor can sustain a sense of continuity within the organization and instill a sense of connectivity with employees’ shared past.” There is frequently a temptation to focus on things that need change, which invariably there are…and which invariably you will hear from people who are happy to find a willing new ear to listen to them. But this posture of acknowledge/embrace is especially true in my case, where my predecessor is the founder and 25-year CEO who continues on as our active chairman.

I know there are a ton of books like this on the market, and while I’ve only read this one, I’d say that if you’re starting a new CEO or executive-level job, this is a good one to at least skim to get some ideas.

(This is going to be an interesting week.  I expect in a couple days, a group of friends and former Return Path colleagues and I are going to officially start a new company once initial funding closes.  I will write about that down the road, but first, this message brought to you by COVID-19.)

I just returned from spending an intense two weeks in Denver.  On March 15, my long-time friend and Board member Brad Feld called me with an interesting idea.  His friend, Colorado Governor Jared Polis (who I’d met a briefly couple times over the years), had an idea of starting and rapidly scaling up a task force in the state government and wanted to tap a private sector entrepreneur to lead the effort.  After some back and forth over 36 hours, and strong encouragement from Mariquita to go help despite the pending lockdown at home in New York, I decided to jump on a plane and go do it. Here’s the description of the group, called the Innovation Response Team (IRT) that I wrote up on LinkedIn:

Governor Jared Polis established the state of Colorado’s COVID-19 Innovation Response Team (IRT), and I was its initial leader to get it off the ground. The team is responsible for pulling together rapid-response creative programs as part of the state’s response to the pandemic that require entrepreneurial, out-of-the-box thinking and deep connections to the private sector (as well as cross-agency within various levels of government), integrated with the state’s Emergency Operations Center. Along with two key deputies from state government, I was responsible for starting the group, both the public sector and private sector sides; recruiting the state team, a leader for the private sector side, and a long-term replacement for myself; and leading the development of the group’s structure, workstreams, and initial plans along with the rest of the team. In the first two weeks, the team grew from 0 to over 200 people (including an army of private sector volunteers) and started to make a significant impact on the state’s response to the crisis.

At Brad’s suggestion out of the gate, I took daily notes as the project unfolded.  I thought the most interesting way to present the experience here on OnlyOnce (because you *definitely* Only lead a COVID-19 state emergency task force Once) would be to share the daily chronicle, a few days at a time, along with a couple photos I took along the way.  So I’ll do that here, then at the end, I’ll do a wrap-up post that compares the work to running a private sector company.  Because the pace of news around COVID-19 is moving so fast, I’ll post a few days’ worth of daily notes at a time.

Sunday, March 15 – Day -1

• Brad text/call to ask me if I’m interested in doing this
• Lukewarm – not excited about leaving home for 2-4 weeks
• Mariquita encourages me to do it – “when else are you going to get an opportunity to have an impact like this?”
• Jared (Governor) called (spoke a mile a minute), outlined his vision and a couple potential workstreams and discussion ends with “talk tomorrow”
• Can’t sleep – started a Google doc in bed with notes on the first workstreams

Monday, March 16, Day 0

• More back and forth with Jared and his team – Lisa (Chief of Staff) and Stan (supervising cabinet member)
• Officially invited to come at 3 pm
• Kids bummed but supportive
• By 6 pm, packed, cleaned up odds and ends at home and was in a car to Kennedy
• 8 pm flight and airport both still ⅔ full 
• Feeling full of purpose
• Worked on more reading and enhanced doc and Day 1 goals
• Texted Brad:  “Thank you. Wish me luck. I don’t know what the fuck I’m doing. Fortunately I never have and that’s usually been ok.”  Brad LOL.
• Notified parents…a bit shocked
• Good to see and surprise Khalid, the driver we used for years at Return Path
• Crashed in extended stay hotel

Stay tuned for more tomorrow! Apologies if any of these notes or posts aren’t quite right…anyone who was there doing the work with me, please send me any corrections you’d like me to post!

One of the new sections in the Second Edition (order here) that I’m excited to share is a deep dive with several chapters on selling your company.  The next few blog posts will share some of my thinking on the subjects as they’re arranged into chapters in the book.  For many startup CEOs the culmination of their life’s work is an exit of some kind (other than being fired!). Personally, there were a range of emotions surging through me when we got to the point of a sale and while the financial reward can be enticing, there are a lot of things that you start to think about, like all the things you created, all the offsites with your team, the good and bad times and, especially, the deep relationships you’ve developed over the years.

If you’re a founder entrepreneur who has led your company for several years, the odds are you have a significant amount of emotional investment in your company, too.  For many entrepreneurs, the company is a deeply embedded part of their identities as a human – right or wrong, for better or for worse. 

I said in the First Edition that entrepreneurship is full of extreme highs and lows and the most difficult thing to accept is when they happen at the same time. Nothing describes the process of selling your company more accurately than that saying because you’re gaining some financial reward, but you’re losing your life’s work. You’re also creating some chaos and uncertainty for all your employees.

One of the most important questions you can ask yourself is, “Am I ready to let go?” For me I used a simple litmus test to help answer that question and I used the answers to these four questions to figure out the sell-don’t sell dilemma:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

You can turn these questions into a scale if you want to be more sophisticated but there are two important points: one, you have to do it and two, you have to look at all four questions as really just providing one piece of information. If I walked into an executive team meeting and said, “I’m not having fun at work,” my team would probably look at me and say (or think to themselves), “Hey, buddy, suck it up.” They’d be right, but if you have low scores on all four questions, that tells a different story. 

So how do you know when it’s time to sell? Usually there’s an inflection point of some kind–either positive or negative. On the positive side, you can receive an out-of-the-blue inbound offer, something you never expected and believe me, that will get the juices flowing! Or maybe when you look two years out you realize that your company is at its highwater mark in valuation, so it becomes a timing issue. Sometimes you can have a major internal problem related to the cap table–a founder with a lot of stock needs liquidity or you need to push this person out of the company. Institutional investors can require liquidity too, and while it’s possible to buy out shareholders or create a debt / equity financing, you might think about selling the company instead.

Other points on selling your company that I make in the Second Edition revolve around who you sell to (financial buyer, strategic buyer) and what the likely outcome of those types of sales are for you and your employees. You’ll need to brace yourself, your team, and your company, and your family for a major impact–the sales process is disruptive, non-linear, and intense and it’s not done until the final agreement is signed. 

Above all else, There is no right or wrong answer here about selling your company.  But there probably is a right or wrong answer for YOU.  That’s the most important thing to think through, deeply, at the early stages of working on selling your company.

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around handling the post-sale transition and integration process.  

No two transitions are exactly the same.  If the buyer is a financial sponsor, you may have the same job the day after the deal closes that you had the day before, just with a new owner and new rules for you.  Sometimes you’ll stay on with a strategic buyer as the head of a division, or the head of your product.  Sometimes you leave on Day 1.  Sometimes you leave later.  

But the most important thing you can do is remember that once the deal is over, it’s over.  That’s why an honest answer to the question, “Are you ready to let go?” that I posed in an early post is so important. You may or may not be the CEO, but now you definitely have a new boss, and in many cases, a boss for the first time in years. And you are no longer in charge.

“Even though the deal was called a merger,” I once heard Ted Leonsis tell the Moviefone founders a while after AOL acquired Moviefone, “please remember that you have been acquired.” Your job is to figure out how best to set your team and products up for success in the new environment, regardless of how long or short you plan to stay at the new company. 

We tried to focus our transition at Return Path to Validity in a few ways:

• For employees, we spent most of our energy and our capital setting things up in the deal documents before closing, recognizing we’d have no control of things after the deal was signed.  Things like how much severance people would get if they were let go, and for how long post-deal, how much their comp could change, whether they could be required to move – those are all things you can negotiate into a deal
• For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years.  Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO.  Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack.  This was a really important way we all got closure on this chapter in our lives
• For the new owners of the business, our objective was to be of service to them, knowing they’d want to run it differently.  So, for example, every time our new owners from Validity asked me a question (“Should we do X or Y,” or “Should we keep person A or person B?”), my answer was never simple. It was always, “What’s your strategy with regard to Z?” and then my advice could be in context, as opposed to thinking about what I would do in the prior context.

There are more details on this in the new section on exits in Startup CEO:  A Field Guide to Scaling Up Your Business.

As I finished up my work on the Second Edition of Startup CEO:  A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons.  The book is called Startup CXO:  A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company?  If you’re leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about?  What does ‘great’ look like?  What challenges lurk around the corner as you scale your function that you might not be focused on today?  If you’re a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people?  If you’re an aspiring executive, from entry-level to manager to director, what do you need to think about as you grow your career and develop your skills?

Startup CXO is a “book of books,” with one section for each major function inside a company.  Each section is be composed of 15-20 discrete short chapters outlining the key “playbooks” for each functional role in the company – Chief People Officer, Chief Financial Officer, Chief Marketing Officer, Chief Revenue Officer, etc., hence the title Startup CXO – which is a generally accepted label in the startup ecosystem for “Chief ____ Officer.”

Here are the front and back covers of the book, with some great endorsements we’re so proud of on the back.

This is an important topic to write about at this particular time because America’s “startup revolution” continues to gather steam.  There are only increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures.  While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books about the topic of Sales, the topic of Product Development), there are very few books that are practical how-to guides for any individual function, and NONE that wrap all these functions into a compendium that can be used by a whole startup executive team.  Very simply, each section of this book serves as a how-to guide for a given executive, and taken together, the book will be a good how-to guide for startup executive teams in general.

Startup CXO has my name on it as principal author, and I’m writing parts of it, but I can’t even pretend to write it on my own, so the book has a large number of contributors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines — most of my Bolster co-founders are writing sections, and the others are being written by former Return Path executive colleagues — Jack Sinclair, Cathy Hawley, Ken Takahashi, Anita Absey, George Bilbrey, Dennis Dayman, Nick Badgett, Shawn Nussbaum, and Holly Enneking.

Startup CXO is also pretty closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent, and as such, the final section of the book has a series of chapters written by Bolster members who are career Fractional Executives about their experience as a Fractional CXO.

The book is available for pre-order now at Amazon and Barnes & Noble.

Oh, and stay tuned for a third book in the series (kind of) due out late this year. More on that over the summer as the project takes shape!

Book Short:  Scrum ptious 

I just finished reading Scrum: The Art of Doing Twice the Work in Half the Time, by Jeff Sutherland and JJ Sutherland. This reading was in anticipation of an Agile Facilitation training my executive team and I are going through next week, as part of Return Path’s  Agile Everywhere initiative. But it’s a book I should’ve read along time ago, and a book that I enjoyed.

Sutherland gets credit for creating the agile framework and bringing the concept scrum to software development over 20 years ago. The book very clearly lays out not just the color behind the creation of the framework, and the central tenets of practice again, but also clear and simple illustrations of its value and benefits.  And any book that employs the Fibonacci series and includes Theodore Roosevelt’s “Man in the Arena” quote — my all-time favorite — is off to a good start by me.

I’ve always appreciated a lot of the underlying philosophy of Agile, such as regularly checking on projects, course correcting in response to feedback from customers or other stakeholders, and working hard to remove any impediments to progress in real time.

One of the author’s most poignant points is that “multitasking makes you stupid.”  I hadn’t focused in the past how agile allows you to clear away context shifts to focus on one task at a time, but that’s another great take away from the book.

Our Agile Everywhere initiative, which is designed to improve productivity across the organization, as well as increase accountability through transparency, is even more critical in my view after having read this book.

The thing that I am left struggling with, which is still very much a work in progress for us, and hopefully something that we will address more head on in our training next week, is the application of the agile framework to teams that are not involved in the production of a tangible work product, such as executive or other leadership teams.  That is something that our Agile Everywhere deployment team has developed a theory about, but it still hasn’t entirely sunk in for me.

I can’t wait for next week’s training session!  If you have any experience applying the agile framework to different types of teams in your company I’d love to hear more about it in the Comments.

(This post also appeared on Bolster.com and builds on last week’s post where I introduced my new startup, Bolster)

Welcome to Bolster, the on-demand executive talent marketplace. We are creating a platform that is the new way to scale an executive team and board.

We believe that startups and scaleups are not average companies. Their rapid growth means their appetite for talent constantly outstrips their budget — and that they can’t spend months searching for it. Their dynamic industries dictate that they keep pace with bigger and better funded competitors. Their leadership teams — the people and the roles — are always changing. Their CEOs spend a ton of time hiring and coaching their leaders and shaping the complexion and direction of the team. They stress out about big expensive new executive hires when sometimes they just need to level-up an existing manager or “try before they buy.” Their Boards frequently jump in to help, but those efforts can be a little ad hoc and inefficient.

We believe that experienced executives working as consultants is the wave of the future. The number of career executives who work flexibly and on-demand for a living is skyrocketing in recent years. People are more often “between things” and are interested in plugging into shorter-term engagements while continuing to look for their next full-time role. People are retiring younger, yet wanting to keep contributing. And even fully-employed execs like to advise companies and serve on Boards. Whether these people are career consultants or are looking for a “side hustle” or just to pay something forward to a future generation of leaders, they all have two common problems: finding work is time consuming and they’re often not good at or don’t like doing it; and managing their back office, everything from insurance to legal to tax to marketing, is a drain on time that could otherwise be spent with clients or family.

We believe that a new kind of talent marketplace is needed to meet the unique and complex requirements of both audiences — the freelance, or flexible, seasoned executive, and the startup or scaleup CEO who thinks holistically about his or her leadership team and carefully tends them like a garden. We are building a platform to make instant, tailored, vetted matches between talent and companies without the randomness of a job board and without the theater, long lead times, and cost, of a full service agency 

Service marketplaces like ours work best when they help their stakeholders solve other meaningful, related problems.In this case, we believe that the need for back office services will help executive consultants focus on more important things. And we believe that CEOs need lightweight and dynamic support in thinking through the composition and skills required of their executive teams both today and 6-18 months in the future.

That is the essence of the business we are building. A business to quickly match awesome companies with awesome freelance executives and to help both sides be better at what they do. We are here to make it easier for you to:

• Bolster your executive team. For our Clients, our pledge to you is that we will quickly and cost-effectively fill the gaps in your leadership ranks (whether interim, fractional, advisory, board, or project-based) with trusted, curated talent, and that we will give you a platform to evaluate your overall leadership team and help you think through your future needs as your company evolves. Think of us as a shortcut to scaling your leadership team.
  
• Bolster your board. The best boards are the ones with multiple independent directors who come from diverse backgrounds with diverse points of view. We also pledge to our Clients that we will find great matches to help fill out their boardrooms as their strategic advisory needs change over time.
  
• Bolster your work. For our Members, our pledge to you is that we will find you the right kind of interesting clients and help you manage your back office so you can focus on your work (and all the other important things in your life!).
  
• Bolster your portfolio. For our Portfolio Partners, VC and PE board members, our pledge to you is that we will make it easier for you and your firm to both drive successful on-demand executive placements for your portfolio company CEOs, and to manage and expand your firm’s network of flexible executive talent. 

We are an experienced team of entrepreneurs and operators who have scaled multiple businesses throughout our careers. All of us worked together as part of the leadership team at Return Path, a leading email technology company that we scaled from 0 to $100mm in revenue and 500 employees in 12 locations around the world while winning numerous Employer of Choice awards. All of us have independent experience scaling other businesses, small and large, public and private. All of us have experience being on-demand executives as well — whether interim, fractional, advisory, project-based, or board roles, we know the landscape of both our members and our clients. 

We’ve all dealt with the stress of having product-market fit and market opportunities but not being able to capitalize on those opportunities because we were missing key talent. And we’ve tried everything from executive search firms (expensive, time-consuming, and slow), to leveling up people (will they be able to grow into the role?), to leaning in to our board (hit or miss, inefficient). Heck, we’ve been desperate enough to follow up on the “my cousin’s boyfriend has an uncle, and he might know someone” lead.

We believe there is a better way for startups and scaleups to find executive talent. Along the way, I published a book about scaling startups called Startup CEO: A Field Guide to Scaling Up Your Business that has sold over 40,000 copies to CEOs around the world. And our whole team is working on a new book called Startup CXO: A Field Guide to Scaling Up Your Teams, which is coming out in early 2021. Our team has a maniacal focus on helping startup teams scale and flourish and on helping leaders develop into the best version of themselves. That’s what we’re all about. 
Plus, we have an amazing group of investors behind us who know how to grow businesses like ours and have incredible reach into the startup and scaleup world. More about that later. For now, we are excited to soft launch Bolster and begin unleashing the power of on-demand executive talent to our Clients. Thank you for being on this journey with us. If you’re interested in the somewhat unusual story of how the company was founded, it’s here.

(This post also appeared on Bolster.com)

As we wrote in our Founding Manifesto, Bolster was started in part to create a new way for startup and scaleup CEOs to think about growing their leadership teams.

Why do CEOs need help with this?

CEOs of any company have too many things to do at all times. This is even more true at startups and scaleups, which by definition are more fast-paced, dynamic, CEO-driven, and thinly staffed. All those challenges point directly to the specific challenge CEOs have with their leadership team.

Think about the journey of a company from a founding team to 50 employees. My long time friend and former board member Greg Sands once compared the phenomenon

of companies growing out of the startup stage to cell development in small organisms. Amoeba or paramecia consist of one cell, and that cell has to do everything: eat, move, sense its surroundings, and respond accordingly. When the cell divides, the new cells still need to do everything – they’re just attached to other cells. As organisms grow more complex, individual cells need to specialize. And when things get really complex, you need a liver, a spleen, a stomach, and a pancreas. By and large, startups work the same way. In the early stages, you have to hire generalists who are both willing and able to take on dozens of tasks at once. Your developers will have to speak with potential customers; your accountants will have to give advice on product direction; and the born salesperson on your team will need to put the phone down a few hours a day and set up a new employee’s computer. That’s a really different team than when you need functional managers on top of engineering, sales, etc. — not to mention needing strategic leadership of those functions as the company grows from 50 to 100 to 250 to 500 employees.

That’s the journey that startup and scaleup CEOs are on. It’s less of a journey and more of a roller coaster ride. Jason is running HR today…but tomorrow, the job of “head of HR” will be different, and Jason might or might not be capable of it. Then your VP Finance Sally gets lured away by an even hotter and sexier new startup and leaves a sudden, gaping hole on your team. Then cracks start to show up with the job Jamie is doing as your marketing director and you lose confidence that your upcoming product launch is going to be a success. Every time one of these events happens – whether it’s an actual event, or just an “aha moment” for you as CEO, you add something to your plate. You add tasks to take over work yourself. You add the task of finding a new person. You add stress from having to deal with one more critical thing.

Leveling up a leadership team is probably the hardest part of the CEO’s job. 

Why don’t current solutions meet the CEO’s needs? Well, of course they do, sometimes. The problem is that the current solutions either aren’t tailored to the needs of startup or scaleup CEOs, or they’re ad hoc and inefficient. Executive search is slow and expensive, and it produces expensive full-time executives. And no matter how good an executive search firm is, I’ve never met a CEO who has a better than 50% success rate in hiring new leaders from the outside. Ever. Add all that up – expensive, slow, medium success rate, and perhaps most important for a startup CEO, leaving you with expensive full-time headcount in multiple areas of your company – that is not a recipe for startup success when you’re sweating your burn rate.

Frequently, the CEO just taps her network for execs or for on-demand executives like the ones Bolster places — that could be asking board members or friends or advisors for suggestions. Quite frankly, those suggestions stand a better chance of success than transactional executive search since the candidate referral source is usually somewhat of an insider. But those searches are really disorganized or one-off. When a CEO turns to their network for spot help, they often aren’t running a comprehensive process, creating a serious job spec, seeing a broad set of candidates for comparisons, and the like. 

Our job at Bolster is to make all of this easier and lighter weight. The rise of the gig economy means that startups no longer need to rely on the painful binary choice of “the person/opening I have today” and “the expensive full-time exec coming in from the outside.”The new way to scale an executive team is with a mix of interim executive talent to quickly fill gaps, fractional executive talent to provide strategic oversight and guidance to a team, part-time, functional mentors/coaches/advisors to advise a less experienced functional leader, project-based consultants to fill in specific holes, and yes, the occasional full-time outside hire, possibly via a search firm (or if your fractional CXO loves your company and joins full-time!). 

With Bolster, you have a network of all those types of talent, well curated and well profiled, available for near-instant matches and near-instant start dates – and a suite of tools and services designed to help you proactively identify your needs across all your functional areas so you’re never scrambling your way out of a tight spot.

What about the existing team? If you’re a leader inside a startup or scaleup, Bolster is ALSO created for you. The painful binary choice CEOs face that I wrote above is particularly painful for you if you’re no longer scaling quickly enough. Frequently, promising junior people are layered or shuttered aside because the CEO doesn’t have the time, or the functional expertise required, to coach or mentor the person to success. Bolster creates an easy mechanism for CEOs to help pinpoint the areas in which you need growth and development as well as an easy way to find either temporary leadership or a function-specific advisor/mentor/coach to help you grow with the role and with the company.

The best startup CEOs I know are the ones who are already using multiple types of on-demand talent at the same time to help their companies along that journey from single-cell to complex organisms. I believe three years from today, the frequent usage of this kind of talent will move from the realm of early adopters to mainstream. The ones who embrace it first will have a competitive advantage.

As we wrote in Bolster’s Founding Manifesto, one of the reasons we started Bolster was to create a new way; a faster, easier, and more cost-effective way, for startup and scaleup CEOs to grow their boards of directors and make them more diverse.

There’s a lot of research out there that the more independent a board is, the better it performs for companies — and that there’s a high degree of correlation between more independent boards and higher performing companies as well. There’s also a lot of research out there that shows that teams which have diversity of gender and race/ethnicity perform better. And everyone who has ever been on a high-functioning board of directors knows that a board is a team.

These facts are well known, yet it is still the case that most private company boards are overwhelmingly made up of founders and investors who are still largely white and male. I believe that the lack of independence and diversity on boards is a big miss for the whole startup ecosystem, and it’s a part of the startup game that we at Bolster want to help change.

Startup boards are tricky things. One of the very unique aspects of a CEO’s job that sets it apart from other executive positions is building and leading a board of directors. But most startup CEOs have either little or no experience building and leading a board, so that part of the job tends to default to a “because that’s the way I assume it’s always been done” kind of task. Of course, if you’re not intentional about building and managing a board, you’re likely to get lousy results. 

Building, shaping, and leading a world class board is one of the single most important things startup CEOs can do to help their businesses thrive and become industry leaders. It’s on par with building and leading an executive team. I’ve seen amazing companies held back by weak and ineffective boards and investor syndicates, and I’ve seen so-so companies succeed because the strategic advice, experience, and accountability coming out of the board room drives the management team in extraordinary ways.

So how is Bolster helping startup CEOs change the game with respect to Boards? We are doing three things. 

First, as you know, what gets measured gets managed. Our first-of-its-kind Board Benchmark application will soon produce an industry standard set of data around private company boards. You can’t find data on private company boards but we’ll soon have important data like size, composition (independents/management/investors), independent director compensation and diversity (gender/race-ethnicity/age). This will help answer questions that I know I have had many times over the years as a CEO such as 

• How big should my board be at this stage? 
• How many independent directors should I have? 
• What is the right profile of an independent director? 
• How many options should I give a board member? 

Starting next week, we’re opening up our Board Benchmark application to any company who creates a free Bolster account. It will tell us a lot about the baseline across the ecosystem, and it will answer a lot of questions startup and scaleup CEOs have but can’t get answers to. Although this is an ongoing real-time benchmark tool, I’ll post some results here when we have enough critical mass to start reporting out.

Second, Bolster is in the talent business, and helping match VC-backed companies with a strong diverse slate of board candidates who are well-matched with their company is at the core of our business. We are already working on many searches for independent board members, and we’ll only be doing more of them as our client base and member base grow.

Finally, this blog post is the beginning of a whole series of posts about startup boards that we hope will demystify them a bit and help change the world’s thinking about how to grow them. Some of the material I will borrow from other blog posts I’ve written, or from the Board of Directors section of Startup CEO. Some will come from other influential VC and CEO bloggers and from Brad Feld and Mahendra Ramsinghani’s book Startup Boards. But much of the content will be new. And because Bolster is a two-sided marketplace, roughly half of the content will be aimed at startup CEOs and the other half at executives who are interested in serving on boards and aren’t sure how to get from where they are today into a board room. We’ll be sending out all the CEO posts as an eBook to CEOs who complete the Board Benchmark study, and all the Member posts as an eBook to Bolster members who fill out their Board profiles. I’ll post both of those eBooks here eventually as well.

For CEOs, the topics we will cover include 

• The purpose of a board
• Size and composition on boards
• Board evolution & turnover
• Diversity in the boardroom and the importance of appointing first-time directors
• What to look for in a director
• How to recruit and interview directors
• How to onboard directors, especially first time directors
• How to compensate directors
• How to build a director bench or Advisory Board
• How to evaluate your board

For executives searching for a board role, the topics we will cover include 

• What startup corporate boards look like
• How to prepare yourself to get on your first board
• Should you serve on an advisory board?
• How to interview for a Board role
• What you need to know about board compensation
• How to approach your first board meeting
• How to think about corporate governance as a board member
• How to be a great board member
• How to give advice or difficult feedback as a board member
• Making sure your voice is heard during a board meeting
• How to know if you’re doing a good job as a board member

We believe that boards can make or break a company and we intend to chart a new course for startup boards. I look forward to sharing thoughts and data with you on that topic in the weeks to come.