Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

Opportunity Knocks

When our friends at Habeas announced that they were exploring a sale of the company a few months back, we were intrigued.  While fiercely competing in the marketplace does create some degree of tension or even mistrust between two companies, that activity also creates a lot of common ground for discussion about the market and the future.

So we are very excited today to announce that we are acquiring Habeas in a deal that is signed and should close within a couple weeks.  Cutting through all the PR platitudes, here’s what this deal really means for our stakeholders:

For everyone we work with, this deal means we have even more scale.  More scale is a good thing.  It means we can invest more in our future in everything from technical infrastructure, to product innovation, to globalization, to employee development.  It’s easy to be great when you’re a 25 person company.  It’s actually quite challenging when you’re a 50-100 person company.  It becomes easier again, though in different ways, when you are a 200 person company with more resources.

For ISPs and filters, more scale means more and better data products to help fine tune filtering algorithms and improve member experience.  It also means an even more streamlined way to reach masses of marketers and publishers. 

For sender clients, we can now offer expanded service levels and access to a broader “footprint” of ISPs and filters who subscribe to our services.  The consolidated company will be one step closer to providing a universal set of standards for measuring sender-focused email quality and reputation.  Some of the details still need to be worked out here, so look for more specific communication from your account representative in the coming weeks.  The one thing we do know at this point is that we will be maintaining both Sender Score Certified and the Habeas SafeList as separate and distinct whitelist programs indefinitely.  So for now, it’s business as usual.

For employees, combining the resources of the two companies means we will be in a better position to wow our clients.  A bigger employee base and a larger company also means more career opportunities for all. 

We have always been mindful that, even as the market leader, we have to earn “every dollar, every day” from our clients, and we have to constantly demonstrate to ISPs and filters that we are not just advocating for our sender clients but for them and their subscribers as well.  None of that changes with this deal.  We still have plenty of competition and are redoubling our efforts to lead the market with innovation and service levels, not just with size and scale.

Our friend Ken Magill wrote some unkind remarks about Habeas a while back.  At the time, as fierce competitors with Habeas, we probably agreed with him.  But as we’ve gotten to know Habeas better over the past few weeks, we realized what a great business the Habeas team has built in the last five years  — including: a strong customer base and partner network, innovative reputation technologies, complementary receiver and data partnerships and most importantly, an incredible team of people as fanatical about saving email as Return Path. For Return Path employees and clients, we get access to these new assets that now makes us an even stronger leader in this space.  And Habeas employees and clients now have expanded access to great resources and talent from Return Path.  But the big winners are the ISPs, filters, and email senders – they will l now have access to a more universal solution to deliverability and filtering accuracy.

So, to  Habeas’ employees, we say “Welcome to the Return Path family!”  We are delighted to have you and look forward to many years of success together.  As I said to my wife when we were in the middle of all the due diligence on the deal, “learning more about Habeas is a little bit like looking in one of those Fun House mirrors at a carnival – you see yourself, just looking slightly different.”  We will all have to work together to move to the common ground from the prior world of competing against each other, but the exciting future of the business and the industry will propel us there. 

Onward!

Building the Company vs. Building the Business

I was being interviewed recently for a book someone is writing on entrepreneurship, which focused on identifying the elements of my “playbook” for entrepreneurial success at Return Path.  I’m not sure I’ve ever had a full playbook, though I’ve certainly documented pieces of it in this blog over the years.  One of the conversations we had in the interview was around the topic of building the company vs. building the business.

The classic entrepreneur builds the business — quite frankly, he or she probably just builds the product for a long time first, then the business.  In the course of the interview, I realized that I’ve spent at least as much energy over the years building the company concurrently with the product/business.  In fact, in many ways, I probably spent more time building the company in the early years than the business warranted given its size and stage.  This is probably related to my theme from a few months ago about building Return Path “Backwards.”

What do I mean by building the company as opposed to building the business?

• Building the business means obsessing over things like product features, getting traction with early clients, competition, and generating buzz
• Building the company means obsessing over things like HR policies, company values and culture, long-term strategy, and investor reporting

In the early years, I did some things that now seem crazy for a brand new, 25-person company, like designing a sabbatical policy that wouldn’t kick in until an employee’s 7th anniversary.  But I don’t regret doing them, and I don’t think they were wasted effort in the long run, even if they were a little wasted in the short run.  I think working on company-building early on paid benefits in two ways for us:

1. They helped lay the groundwork for scaling – what we’re finding now as we are trying to rapidly scale up the business, and even over the last few years since we’ve been scaling at a moderate pace, is that we are doing so on a very solid foundation
2. The company didn’t die when the product and business died – because we had built a good company, when our original ECOA business basically proved to be a loser back in 2002, it was a fairly obvious decision (on the part of both the management team and the venture syndicate) to keep the business going but pivot the business, more than once

Starting about four years ago, for the first time, I felt like we had a great business to match our great company.  Now that those two things are in sync, we are zooming forward at an amazing pace, and we’re doing it perhaps more gracefully than we would be doing it if we hadn’t focused on building the company along the way.

I’m not saying that there’s a right path or a wrong path here when you compare business building with company building, although as I wrote this post, my #2 conclusion above is a particularly poignant one, that without a strong company, we wouldn’t be here 12 years later.  Of course, you could always argue that if I’d spent more time building the business and less time building the company, we might have succeeded sooner.  In the end, a good CEO and management team must be concerned about getting both elements right if they want to build an enduring stand-alone company.

New Media’s Influence on the Traditional

Last week, DMNews unveiled its new look and feel and format (of the print publication) at the DMA’s annual convention in Chicago.  Hats off to Publisher Julia Hood and Editor-in-Chief Elly Trickett for diving in and coming up with some great improvements to the publication so quickly after taking the reigns.

What I find particularly interesting about the new format is that its design and even content structure seem to borrow heavily from the world of online media,  such as:

• A top-of-page “navigation bar” that tells you at a glance what articles are on the page (email, circulation, multichannel, legislation, lists, etc.) so you can flip pages and figure out quickly where to stop based on your interests
• MUCH shorter news briefs
• More “fixed” topic sections that are (I think) meant to be recurring in every issue…”Gloves off,” “Duly noted,” “Nailed it”
• “Key points” call-outs of an article etc. instead of all the long form of the prior generation of the publication
• A section called “data bank” that is almost like an analytics widget

I had been ignoring the print edition for several months, assuming I’d catch any critical articles to me via the web site, keyword feeds, and the email newsletter.  But this new format will definitely have me back to at least flipping through the print edition looking for relevant articles.

People are People

So after nearly seven years of running Return Path, I think it’s now fair to say that I’m a direct marketer.  I’ve learned a lot about this business over the years, and there are a number of things about direct marketing that are phenomenal — the biggest one is that most of the business is incredibly clear, logical, and math-driven.  But there’s always been one thing about the field that hasn’t quite made sense to me, and I think it’s because the Internet is once again changing the rules of the game.

There are traditional companies in the space that focus on B2C direct marketing.  There are others that focus on B2B.  It’s been obvious to me for years that there was a huge cultural or perceived divide between these types of companies.  You can see it in the glazed over eyes and hear it in the scratchy voices of long-time industry members from the postal and telemarketing world — "Ohhh," they say, "they’re a B2B company.  We don’t do that."

But the distinction between B2B and B2C is rapidly diminishing.  I may not want a telemarketing call about office supplies on my home number or one about car insurance at work (or any of them at all!).  It might not make sense to send me a catalog for routers to my home.  I get that.  But at the end of the day, people are people, and the ubiquity of the Internet is eroding distinctions between the different places I spend time. 

True, most of us do have multiple email addresses, and some are company-sponsored while others are personal.  But how many of us have all that email coming into the same mailbox in Outlook?  Or if we do have a Yahoo or Hotmail or Gmail account, how many times per day do we check it from the office?  Is an @aol.com account a B2C account?  I don’t know – AOL says there are hundreds of thousands of small businesses who use AOL.  Is an @ibm.com account a B2B account?  It’s probably someone’s work account, but how many times does he check that account on his Treo over the weekend?  And what if it’s that person’s only email address?

Sure, you’ll want to use different media properties or lists to acquire corporate buyers vs. individuals.  Sure, there are still some nuances of data collection in the distinction as well (no reason for LL Bean to ask you for your title), and there will always be differences in creative and copy to drive response for a corporate buyer vs. a personal buyer.  But the legacy distinctions between B2C and B2B are definitely melting away.

So I’m not accused of being Internet-myopic, this same principle (or a related one) explains why you see ads like crazy for FedEx and DHL during The Office on NBC.  I had this quote written down from several months back for which unfortunately I don’t have attribution, although I’m pretty sure it was a media buyer in a Wall Street Journal article, who said, "The best time you can reach people is when they’re in their entertainment mode and consuming media they really want to see when they’re in their down time.  And that might not be CNBC, that might be My Name is Earl on NBC."

As I mentioned earlier this summer, I’ve been working on a new startup the past few months with a group of long-time colleagues from Return Path.  Today, we are officially launching the new company, which is called Bolster.  The official press release is here.

Here’s the business concept.  Bolster is a talent marketplace, but not just any talent marketplace.  We are building a talent marketplace exclusively for what we call on-demand (or freelance) executives and board members.  We are being really picky about curating awesome senior talent.  And we are targeting the marketplace at the CEOs and HR leaders at venture- and PE-backed startups and scaleups.  We’re not a search firm.  We’re not trying to be Catalant or Upwork.  We’re not a job board. 

To keep both sides of the marketplace engaged with us, we are also building out suites of services for both sides – Members and Clients.  For Members, our services will help them manage their careers as independent consultants.  For Clients, our services will help them assess, benchmark and diversify their leadership teams and boards. 

We have a somewhat interesting founding story, which you can read on our website here.  But the key points are this.  I have 7 co-founders, with whom I have worked for a collective 88 years — Andrea Ponchione, Jack Sinclair, Shawn Nussbaum, Cathy Hawley, Ken Takahashi, Jen Goldman, and Nick Badgett.  We have three engineers with whom we’ve worked for several years who have been on board as contractors so far – Kayce Danna, Chris Paynes, and Chris Shealy.  We have four primary investors, who I’ve also known and worked closely with for a collective 77 years — High Alpha and Scott Dorsey (another veteran of the email marketing business), Silicon Valley Bank and Melody Dippold, Union Square Ventures and Fred Wilson, and Costanoa Ventures and Greg Sands.  Pretty much a Dream Team if there ever was one.

So how did our team and I get from Email Deliverability to Executive Talent Marketplace?  

It’s more straightforward than you’d think.  If you know me or Return Path, you know that our company was obsessed with culture, values, people, and leadership development.  You know that we created a cool workforce development nonprofit, Path Forward, to help moms who have taken a career break to care raise kids get back to work.  You know that I wrote a book for startup CEOs and have spent tons of time over the years mentoring and coaching CEOs.  Our team has a passion for helping develop the startup ecosystem, we have a passion for helping people improve and grow their careers and have a positive impact on others, and we have a passion for helping companies have a broad and diverse talent pipeline, especially at the leadership level.  Put all those things together and voila – you get Bolster!

There will be much more to come about Bolster and related topics in the weeks and months to come.  I’ll cross-post anything I write for the Bolster blog here on OnlyOnce, and maybe occasionally a post from someone else.  We have a few opening posts for Bolster that are probably running there today that I’ll post here over the next couple weeks.

If you’re interested in joining Bolster as an executive member or as a client, please go to www.bolster.com and sign up – the site is officially live as of today (although many aspects of the business are still in development, in beta, or manual).

The Good, The Board, and The Ugly, Part III

To recap other postings in this series:  my original, Brad Feld’s, Fred Wilson’s first, Fred’s second, Tom Evslin’s, and my lighter-note follow-up.

So speaking of lighter-note takes on this topic, Lary Lazard, Tom Evslin’s fictional CEO who ran Hackoff.com, now has his own tips for effective board management.  You have to read them yourself here, but I think my favorite one is #3, which starts off:

Never number the pages of what you are presenting.  Lots of time can be used constructively figuring out what page everybody is on.

Enjoy.

Counter Cliche:  How Much Paranoia is Too Much Paranoia?

Fred’s VC cliche of the week this week, Opening the Kimono, is a good one.  He talks about how much entrepreneurs should and should not disclose when talking to VCs and big partners — companies like Microsoft or Google, for example.

In response to another of Fred’s weekly cliche postings back in April, I addressed the issue of opening the kimono with VCs in this posting entitled Promiscuity.  But today’s topic is the opposite of promiscuity, it’s paranoia.

I was talking with a friend a few months back who’s a friend and fellow CEO of a high profile, larger company in a similar space to Return Path.  He was obsessing about the secrecy surrounding the size of his business and wouldn’t tell me (a friend) how much revenue his company had, even within a $20mm band.

He pursued this secrecy pretty far.  He never shared financials with his employees.  He never told anyone the metrics, not even his close friends and family.  He even withdrew his company from consideration for a high-profile award for growth companies which it had entered into and won in prior years since someone might be able to string together enough years of data to compute their size.

Why?  Because he didn’t want any venture capitalists to figure out how big they had gotten and decide to throw money at upstart competitors.  Talk about a closed kimono!

I’m much more open book than that with Return Path, but I have a tremendous amount of respect for this guy, so I gave the matter some thought.  There are certainly some situations which call for discretion, but I couldn’t come up with too many that would drive my guiding principle to be secrecy.

1. Being “open book” with employees is essential.  Your people need to know where the business stands and how their efforts are contributing to the whole.  More important, they need to know that you trust them.

2. Using some key metrics to promote your company can be very helpful.  I challenge you to show me a marketing person who doesn’t want to brag about how big you are, how many customers you have, what market share you have.

3. There’s no reason to worry about Venture Capitalists.  Sure, they can fund a competitor, but they’ll do that without knowing exactly how much revenue you have, how quickly.  The good ones are good at sniffing out market opporunities ahead of time.  The bad ones, you care about less anyway.

4. All that said, you can never be paranoid enough about the competition.  Assume they’re all out to get you at every turn, that they’re smarter, richer, quicker, and better looking than you are.  Live in fear of them eating your lunch.

Paranoia is healthy (just ask Andy Grove), but it does have its limits around the basics of your business, and around how you treat employees.

As I mentioned in a previous post, I write a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. I share the column with my colleagues Jack Sinclair and George Bilbrey and we cover how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. I recently posted George’s column on Staying Innovative as Your Business Grows (Part One). Below is a re-post of George’s second part of that column from this week, which I think my OnlyOnce readers will enjoy.

Guest Post: Staying Innovative as Your Business Grows (Part Two)

By George Bilbrey
Last month, as part of the Online Entrepreneur column, I shared some of Return Path’s organizational techniques we use to stay innovative as we grow. In this article, I’ll talk about the process we’re using in our product management-and-development teams to stay innovative.

The Innovation Process at Return Path
As we grew bigger, we decided to formalize our process for bringing new products to market. In our early days we brought a lot of new products to market with less formal process but also with more limited resources. We did well innovating one product at a time without that kind of process largely because we had a group of experienced team members. As the team grew, we knew we had to be more systematic about how we innovated to get less experienced product managers and developers up to speed and having an impact quickly.

We had a few key objectives when designing the process:

• We wanted to fail fast – We had a lot of new product ideas that seemed like good ones. We wanted a process that allowed us to quickly determine which ideas were actually good.

• We wanted to get substantial customer feedback into the process early – We’d always involved clients in new product decisions, but generally only at the “concept” phase. So we’d ask something like “Would you like it if we could do this thing for you?” which often elicited a “Sure, sounds cool.” And then we’d go off and build it. We wanted a process that instead would let us get feedback on features, function, service levels and pricing as we were going so we could modify and adjust what we were building based on that iterative feedback.

• We wanted to make sure we could sell what we could build before we spent a lot of time building it – We’d had a few “build it and they will come” projects in the past where the customers didn’t come. This is where the ongoing feedback was crucial.

The Process
We stole a lot of our process from some of the leading thinkers in the “Lean Startup” space – particularly Gary Blanks’ Four Steps to the Epiphany and Randy Komisar’s Getting to Plan B. The still-evolving process we developed has four stages:

Stage 1: Confirm Need

Key Elements

• Understand economic value and size of problem through intense client Interaction
• Briefly define the size of opportunity and rough feasibility estimate – maybe with basic mockups
• Key Question: Is the need valid? If yes, go on. If no, abandon project or re-work the value proposition.

Stage 2: Develop Concept

Key Elements

• Create a high fidelity prototype of product and have clients review both concept and pricing model
• Where applicable, use data analysis to test feasibility of product concept
• Draft a more detailed estimate of effort and attractiveness, basically a business model
• Key Question: Is the concept Valid? If yes, go on. If no, abandon project.

Stage 3: Pilot

Key Elements

• Build “minimum viable product” and sell (or free beta test with agreed to post beta price) with intense client interaction and feedback
• Develop a marketing and sales approach
• Develop a support approach
• Update the business model with incremental investment requirements
• Preparation of data for case studies
• Key Question: Is project feasible? If yes, go on. If no, abandon project or go back to an earlier stage and re-work the concept.

Stage 4: Full Development and Launch

Key Elements

• Take client feedback from Pilot and apply to General Availability product
• Create support tools required
• Create sales collateral, white papers, lead generation programs, case studies and PR plan.
• Train internal teams to sell and service.
• Update business model with incremental investment required
• Go forth and prosper

There are a several things to note about this process that we’ve found to be particularly useful:

• A high fidelity prototype is the key to getting great customer feedback – You get more quality feedback when you show them something that looks like the envisioned end product than talking to them about the concept. Our prototypes are not functional (they don’t pull from the databases that sit behind them) but are very realistic HTML mockups of most products.

• Selling the minimum viable product (MVP) is where the rubber meets the road – We have learned the most about salability and support requirements of new products by building an MVP product and trying to sell it.

• Test “What must be true?” during the “Develop Concept” and “Pilot Phases” – When you start developing a new product, you need to know the high risk things that must be true (e.g., if you’re planning to sell through a channel, the channel must be willing and able to sell). We make a list of those things that must be true and track those in weekly team meetings.

• This is a very cross functional process and should have a dedicated team – This kind of work cannot be done off the side of your desk. The team needs to be focused just on the new product.

While not without bumps, our team has found this process very successful in allowing us to stay nimble even as we become a much larger organization. As I mentioned in Part 1, our goal is really to leverage the strengths of a big company while not losing the many advantages of smaller, more flexible organizations.

I’ve published two editions of Startup CEO, a sequel called Startup CXO, and am a co-author on the second edition of Startup Boards. We also just (2025) published mini-book versions of Startup CXO specifically for five individual functions, Startup CFO, Startup CRO, Startup CMO, Startup CPO, and Startup CTO.

You’re only a startup CEO once. Do it well with Startup CEO, a “master class in building a business.”

—Dick Costolo, Partner at 01A (Former CEO, Twitter)

Being a startup CEO is a job like no other: it’s difficult, risky, stressful, lonely, and often learned through trial and error. As a startup CEO seeing things for the first time, you’re likely to make mistakes, fail, get things wrong, and feel like you don’t have any control over outcomes.

As a Startup CEO myself, I share my experience, mistakes, and lessons learned as I guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees.

Startup CEO is not a memoir of Return Path’s 20-year journey but a CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that startup CEOs will face.

You’ll learn:

How to tell your story to new hires, investors, and customers for greater alignment How to create a values-based culture for speed and engagement How to create business and personal operating systems so that you can balance your life and grow your company at the same time How to develop, lead, and leverage your board of directors for greater impact How to ensure that your company is bought, not sold, when you exit

Startup CEO is the field guide every CEO needs throughout the growth of their company and the one I wish I had.

“Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career.”

– Scott Dorsey, Managing Partner, High Alpha (Former CEO, ExactTarget)

One of the greatest challenges for startup teams is scaling because usually there’s not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. My team and I understand the scaling challenges—we’ve been there, and it took us nearly 20 years to scale and achieve a successful exit. Along the way we learned what worked and what didn’t work, and we share these lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a “CEO to CEO Advice” summary from me on what great looks like for that CXO, signs your CXO isn’t scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

A comprehensive guide on creating, growing, and leveraging a board of directors written for CEOs, board members, and people seeking board roles.

The first time many founders see the inside of a board room is when they step in to lead their board. But how do boards work? How should they be structured, managed, and leveraged so that startups can grow, avoid pitfalls, and get the best out of their boards? Authors Brad Feld, Mahendra Ramsinghani, and Matt Blumberg have collectively served on hundreds of startup and scaleup boards over the past 30 years, attended thousands of board meetings, encountered multiple personalities and situations, and seen the good, bad, and ugly of boards.

In Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, the authors provide seasoned advice and guidance to CEOs, board members, investors, and anyone aspiring to serve on a board. This comprehensive book covers a wide range of topics with relevant tips, tactics, and best practices, including:

• Board fundamentals such as the board’s purpose, legal characteristics, and roles and functions of board members;
• Creating a board including size, composition, roles of VCs and independent directors, what to look for in a director, and how to recruit directors;
• Compensating, onboarding, removing directors, and suggestions on building a diverse board;
• Preparing for and running board meetings;
• The board’s role in transactions including selling a company, buying a company, going public, and going out of business;
• Advice for independent and aspiring directors.

Startup Boards draws on the authors’ experience and includes stories from board members, startup founders, executives, and investors. Any CEO, board member, investor, or executive interested in creating an active, involved, and engaged board should read this book—and keep it handy for reference.

Five new mini-books from Startup CXO, but with new bonus material and an obvious focus on each specific functional area.

Each book has several topics in common – chapters on the nature of an executive’s role, how a fractional person works in that role, how the role works with the leadership team, how to hire that role, how the role works in the beginning of a startup’s life, how the role scales over time, and CEO:CEO advice about managing the role.

In Startup CTO (Technology and Product), the role-specific topics Shawn Nussbaum talks about are The Product Development Leaders, Product Development Culture, Technical Strategy, Proportional Engineering Investment and Managing Technical Debt, Shifting to a New Development Culture, Starting Things, Hiring Product Development Team Members, Increasing the Funnel and Building Diverse Teams, Retaining and Career Pathing People, Hiring and Growing Leaders, Organizing Collaborating with and Motivating Effective Teams, Due Diligence and Lessons Learned from a Sale Process, Selling Your Company, Preparation, and Selling Your Company/Telling the Story.

In Startup CMO, the role-specific topics Nick Badgett and Holly Enneking talk about are Generating Demand for Sales, Supporting the Company’s Culture, Breaking Down Marketing’s Functions, Events, Content & Communication, Product Marketing, Marketing Operations, Sales Development, and Building a Marketing Machine.

In Startup CFO, the role-specific topics Jack Sinclair talks about are Laying the CFO Foundation, Fundraising, Size of Opportunity, Financial Plan, Unit Economics and KPIs, Investor Ecosystem Research, Pricing and Valuation, Due Diligence and Corporate Documentation, Using External Counsel, Operational Accounting, Treasury and Cash Management, Building an In-House Accounting Team, International Operations, Strategic Finance, High Impact Areas for the Startup CFO as Partner, Board and Shareholder Management, Equity, and M&A.

In Startup CRO, the role-specific topics Anita Absey talks about are Hiring the Right People, Profile of Successful Sales People, Compensation, Pipeline, Scaling the Sales Organization, Sales Culture, Sales Process and Methodology, Sales Operating System, Marketing Alignment, Market Assessment & Alignment, Channels, Geographic Expansion, and Packaging & Pricing.

In Startup CPO (HR/People), the role-specific topics Cathy Hawley talks about are Values and Culture, Diversity Equity and Inclusion, Building Your Team, Organizational Design and Operating Systems, Team Development, Leadership Development, Talent and Performance Management, Career Pathing, Role Specific Learning and Development, Employee Engagement, Rewards and Recognition, Reductions in Force, Recruiting, Onboarding, Compensation, People Operations, and Systems.

Wanted!  Comp Benchmark Participants

Return Path is looking to benchmark our compensation structure with those of peer companies.  We would like to organize a project where an independent consultant gathers and compiles the data from a group of 10-20 companies and shares the aggregated results with individual benchmarks back with participants (the data will be anonymous on a per-company basis). 

The data we’d need from participating companies (for all positions) is:  Title and summary of the job description; Base Salary; Bonus; and Location.

The criteria for "peer company" is one that is comparable in size (50-250 people), geography (not rural, at least some in NY/Chicago/SF/LA), and industry (anything tech/Internet/services).

We will act as the project manager.  Participating companies will mainly just have to provide the data.  The cost of the consultant will be approximately $1,000-2,000 per participating company.  This is a small fraction of what a similar study would cost from one of the big HR/benefits consultancies — and should be much more targeted and useful as well.

If you are interested in participating please email us at [email protected].  VCs out there — please circulate this to your CEOs and CFOs!