(Post 4 of 4 in the series on Scaling CROs – other posts are, When to Hire your First Chief Revenue Officer, What Does Great Look like in a Chief Revenue Officer and Signs your Chief Revenue Officer isn’t Scaling)

Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent.

One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events.  Particularly if you’re a B2B company that engages with clients during the sales process, you’ll probably find yourself at a lot of client meetings and events, either internal or external.  Your CRO will be there, too, which gives you a great opportunity to spend large blocks of time together in transit, or a good deal of time together socially. One thing we learned during the work-at-home pandemic is just how much time we save by not traveling.  So when life resumes to normal, why waste time in an Uber or on a plane when you can have a deep strategic conversation or even a personal/social one with one of your senior executives? Of course, you have to actually be more proactive in meeting with your CRO since you won’t have events that naturally bring you together, but I’ve found that the early morning time in the hotel gym or late-night drink in the lobby bar before heading up to bed now translates to time I can have with my CRO. 

Another way to engage with the CRO is In a Weekly Forecast meeting.  Jeff Epstein, former CFO of Oracle, was one of my long-time board members at Return Path and he helped us architect a new core business process once our sales team got large and mature and geographically disparate enough that it was hard for us to have a solid forecast.  Both me and our CFO engaged in the Weekly Forecast meeting and because of that we forced the discipline of a good roll-up of all regions and business units. The CRO and all sales managers attended and knew that we were paying attention to the numbers and trends and asking tough questions. Our attendance was a forcing function for the CRO so that they organized a pre-meeting the prior day with all teams and units to prepare, and that in and of itself had a cascading effect through the organization of adding discipline, rigor, and accuracy to the forecast.  It also made me a lot more empathetic to my CRO’s issues with respect to the sales leadership team.

Finally, the other way that I engaged with the CRO was ad hoc, either internally or in-market.  My most successful heads of sales have been good at winding me up and pointing me at things as needed, whether that means getting on a plane or Zoom to help close a deal or save a client, or doing a 1:1 mentoring session with a key employee. So, not all interactions with the CRO have to be initiated by the CEO, and a great CRO will use the CEO, leverage their time, when it’s needed.

(You can find this post on the Bolster Blog here)

(Post 1 of 4 in the series of Scaling CPDO’s).

For most startups the idea of hiring a CBDO is a pipedream, it’s a role that only global corporations have, right? After all, strategic partnerships and M&A are rare events for a startup and can be handled by the founder/CEO, or potentially by someone in Sales.  If a startup is partner or channel heavy, those areas may be the focus of the Sales team in general.  Or, if there is sporadic M&A activity that can be handled by external advisors or bankers. So how do you know when it’s time to hire your first CBDO?

You know it’s time to hire a CBDO when you are spending too much of your own time on things that a CBDO could be doing. When a deal shows up, it’s a mountain of work because there are countless meetings and conversations both internal and external to the company and with your board; there’s a ton of due diligence that needs to be done, and there’s always thinking about the strategic roadmap moving forward. The problem is that you can’t control when a deal shows up but once it does, a series of processes and tasks that are time-dependent kick in and it can consume all of your bandwidth. It’s worth it to hire a CBDO if you think you’re only going to do one deal just to take all that effort off your plate.

Another sign that you should hire a CBDO is if your board asks you for your M&A roadmap, and you don’t have a great answer and aren’t sure how to get to one. For a startup the stratetgic roadmap might just be to grow the company any way they can, but for a scaleup you’ll have to be much more thoughtful about strategic growth, you’ll need to have metrics, benchmarks, and timelines, you’ll need to know whether you can hit those milestones organically or whether you need to partner, acquire, or sell off parts of the business. A CBDO not only thinks about all the nuances of a stratetgic roadmap, but has done the work to make it easy to pull the trigger when the opportunity arises.

A more practical solution for many startups is to consider a fractional CBDO. A fractional CBDO may be the way to go if you need help defining your partnership or M&A strategy, or you need help creating a market map and you don’t want to rely on an external advisor or banker for those. A fractional CBDO can also help execute a couple of M&A transactions that are too small for a banker so if you’re not sure about whether or not a full-time CBDO makes sense for you, you can experiment with smaller deals first. A fractional CBDO could also help define a major new strategic building block like “creating an indirect sales channel” or “international expansion,” and work with you and your whole leadership team together to create that, especially if no one at your company has experience in doing that. 

You can find this post on the Bolster Blog here.

Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!”  I thought about it more after and came up with five reasons why. 

First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here. 

Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.

Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more.  This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different. 

The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in.  When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product.  But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer.  In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product.  At Bolster, we have three user personas — Member, Client, and Partner.  And I’m all three of them.  I’m constantly in the product, multiple times a day.  I’m deeply familiar with all angles of the executive search and board building process.  It’s MUCH better to be this close to the product, and the same is true for many of our team members.

Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic.  I love working with clients.  I love talking to members.  I love advising and coaching CEOs. I love being a pretend product manager.  I love writing marketing copy.  It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)

I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.

Jim Collins, in both Good to Great and Built to Last talked about the BHAG – the Big, Hairy Audacious Goal – as one of the drivers of companies to achieve excellence.  Perhaps that’s true, especially if those goals are singular enough and simplified enough for an entire company of 100-1000-10000 employees to rally around.

I have also observed over the years that both star performers and strong leaders drive themselves by setting large goals.  Sometimes they are Hairy or Audacious.  Sometimes they are just Big.  I suppose sometimes they are all three.  Regardless, I think successfully managing to and accomplishing large personal goals is a sign of a person who is driven to be an achiever in life – and probably someone you want on your team, whether as a Board member, advisor, or employee, assuming they meet the qualifications for the role and fit the culture, of course.

I’m not sure what the difference is between Hairy and Audacious.  If someone knows Jim Collins, feel free to ask him to comment on this post.  Let’s assume for the time being they are one and the same.  What’s an example of someone setting a Hairy/Audacious personal goal?  My friend and long-time Board member Brad Feld set out on a quest 9 years ago to run a marathon in each of the 50 states by the age of 50.  Brad is now 9 years in with 29 marathons left to go.  For those of you have never run a marathon (and who are athletic mortals), completing one marathon is a large, great and noteworthy achievement in life.  I’ve done two, and I thought there was a distinct possibility that I was going to die both times, including one I ran with Brad .  But I’ve never felt better in my life than crossing the finish tape those two times.  I’m glad I did them.  I might even have another one or two in me in my lifetime.  But doing 50 of them in 9 years?  That’s a Hairy and Audacious Goal.

For me, I think the Big goal may be more personally useful than the Hairy or Audacious.  The difference between a Big goal and a Hairy/Audacious one?  Hard to say.  Maybe Hairy/Audacious is something you’re not sure you can ever do, where Big is just something that will take a long time to chip away at.  For example, I started a quest about 10-12 years ago to read a ton of American history books, around 50% Presidential biographies, from the beginning of American history chronologically forward to the present.  This year, I am up to post-Civil War history, so roughly Reconstruction/Johnson through Garfield, maybe Arthur.  I read plenty of other stuff, too – business books, fiction, other forms of non-fiction, but this is a quest.  And I love every minute of it.  The topic is great and dovetails with work as a study in leadership.  And it’s slowly but surely making me a hobby-level expert in the topic.  I must be nearing Malcolm Gladwell’s 10,000 hours by now.

The reason someone sets out on a personal quest is unclear to me.  Some people are more goal-driven than others, some just like to Manage by Checklist, others may be ego-driven, some love the challenge.  But I do think that having a personal quest can be helpful to, as Covey would say, Sharpen the Saw, and give yourself something to focus personal time and mental/physical energy on.

Just because someone isn’t on a personal quest doesn’t mean they’re not great, by the way.  And someone who is on a quest could well be a lunatic.  But a personal quest is something that is useful to look for, interesting and worth learning more about if discovered, and potentially a sign that someone is a high achiever.

Selling a Line of Business

It’s been a couple of years since Return Path decided to focus on our deliverability business by divesting and spinning out our other legacy businesses. That link tells some of the story, and the rest is that subsequently, Authentic Response divested part of the Postmaster Direct business to Q Interactive.  Those three transactions, plus a number of experiences over the years on the buy side of similar transactions (Bonded Sender, Habeas, NetCreations), plus my learnings from talking to a number of other CEOs who have done similar things over the years, form the basis of this post.  The Authentic Response spin-out was also partially chronicled by Inc. Magazine in this article earlier this year.

It’s an important topic — as entrepreneurs build businesses, they frequently end up creating new revenue opportunities and go off on productive tangents.  Those new lines of business might or might not take off; but sometimes they can take off and still, down the road, end up being non-core to the overall mission of the company and therefore candidates for divestiture.  Even if they are good businesses, the overall enterprise might benefit from the focus or cash provided by a sale.  Look at the example of Occipital building the Red Laser app, then selling it to eBay to finance the rest of their business.

Here are some of the signs of a successful divestiture:

• Business is truly non-core or relies on starkly different competencies for success (e.g., one is B2B, the other is B2C)
• Business is growing rapidly and requires assistance to scale properly (either technology, or sales)
• Business has its own culture and operations and “a life of its own”

Conversely, here are some of the reasons why a divestitures of a business unit might stall or fail:

• Lack of a very compelling story as to why you’re selling the business unit
• Stand-alone financials of the unit are too hard for the buyer to determine with confidence
• Operations of the unit too tethered to the mothership
• There is some problem with the leadership of the unit (there is no stand-alone leader, the leader isn’t involved in the divestiture, the leader isn’t squarely behind the divestiture)
• Business performance weakens during the process

I have a couple points of advice to entrepreneurs in this situation.  The first is to clarify for yourself up front:  are you selling a true line of business, or are you selling assets?  If you are selling assets, you need to clearly define what they are, and what they aren’t, and you need to make sure all legal details (contracts, IP, etc.) are buttoned up before the process starts.

If you are selling a true line of business, beware that buyers will not be interested in doing any hard work, or if they feel like they have to do hard work, the price they pay for the business will reflect that in the form of a steep, steep discount.  The financials must be understandable and credible on a stand-alone basis.  The business must be completely separated from the core already.  The business must have its own management team, completely aligned with the decision to sell.

You also have to be extremely cognizant of the human aspects of what you’re doing.  Every culture is different, and I’m not advocating one style over another, but selling or spinning out a business is very different than selling a company.  There’s going to be a big difference in reactions, perceptions, hopes, and fears between the people in the core who are staying, and the people in the business unit that’s going.  Having a heightened awareness of those differences and factoring them into your communications plan is critical to success, as a poorly managed effort can end up harming both sides.

In terms of valuation expectations, don’t expect to get any credit for synergies.  You have to present them and sell them, and they may make the different between getting a deal done and not, but they will most likely not impact the price you get for the divestiture.

Finally, remember that buyers understand your psychology as well.  They know you’re selling the business for a reason (you need to raise cash, you’re concerned about its future performance, it’s become a distraction or has the potential to suck scarce resources out of your core, etc.).  They will completely understand the costs you carry, whether financial, opportunity, or mental, in continuing to own the business.  And they will factor that into the price they’re willing to offer.  Of course, as with all deals, the best thing you can do to maximize price is have multiple interested parties bidding on the deal!

Book Short (and great concept): Moments of Truth

TouchPoints:  Creating Powerdul Leadership Connections in the Smallest of Moments, by Douglas Conant, former CEO of Campbell’s Soup Corporation, and Mette Norgaard (book, kindle), is a very good nugget of an idea wrapped in lots of other good, though only loosely connected management advice around self awareness and communication — something I’m increasingly finding in business books these days.

It’s a very short book. I read it on the Kindle, so I don’t know how many pages it is or the size of the font, but it was only 2900 kindles (or whatever you call a unit on the device) and only took a few Metro North train rides to finish.  It’s probably worth a read just to get your head around the core concept a bit more, though it’s far from a great business book.

I won’t spend a lot of time on the book itself, but the concept echoes something I’ve been referring to a while here at Return Path as “Moments of Truth.”  Moments of Truth are very short interactions between you and an employee that are high impact and, once you get the hang of them, low effort.  At least, they’re low effort relative to long form meetings.

Here are a few thoughts about Moments of Truth:

• They are critical opportunities to get things both very right and very wrong with an employee
• They are more powerful than meets the eye – both for what they are and because they get amplified as employees mention them to other employees
• They can come to you (people popping into your office and the like), you can seek them out (management by walking around), and you can institutionalize them (for example, one of the things I do is call every employee on their Return Path anniversary to congratulate them on the milestone)
• They are no different than any other kind of interaction you have, just a lot shorter and therefore can be more intense (and numerous)
• Their use cases are as broad as any management interaction — coaching, positive or negative feedback, input, support, etc.

What can you as a manager or leader do to perfect your handling of Moments of Truth?

First, learn how to spot them when they come to you, and think about a typical employee’s day/week/month/year to think about when you can find opportunities to seek them out.  Their first day on the job.  When they get a promotion.  When they get a great performance review, or new stock options.  Maybe when they get a poor performance review or denied a promotion they were seeking.

Second, learn to appreciate them and leave space for them.  If you have zero free minutes in every single day, you not only won’t have time to create or seek out Moments of Truth, you’ll be rushed or blow them off when they come to you.

Finally, like everything else, you have to develop a formula for handling them and then practice that formula.  The book does talk about a formula of “head, heart, hand” (e.g., being logical, authentic, and competent) that’s not bad.  Although I’d never thought about it systematically before writing this post, I have a few different kinds of Moments of Truth, and each one has its own rhythm to it, and its own regular ending.

But regardless of how you handle them, once you think about your day through this lens, you’ll start seeing them all over the place.  Recognize their power, and dive in!

Managing in a Downturn

I spoke at a NextNY event last night along with several others, including fellow entrepreneur David Kidder from Clickable and angel investor Roger Enhrenberg about this fine topic (Roger wrote a great post on it here) and thought I’d share a few of the key points made by all of us for anyone trying to figure out what to do tactically now that Sequoia has told us to be afraid, very afraid.

Hope is Not a Strategy:  Your business is not immune. It will do what everyone else’s will. Struggle to hit its numbers. Struggle to collect bills. Lose customers. There is no reason to hope you’ll be different.

Get Into the Jet Stream:  Develop your core revenue streams — and make sure they’re really your revenue, not just skimming tertiary revenue out of the ecosystem.  Investors will look to see how sustainable your model is with more scrutiny than ever.

It’s a Long Road to Recovery:  I don’t care what people say. There is no true “v-shaped” bounceback from a true downturn. Plan for a long (4-8 quarter) time to return to normalcy.

Budget Early and Often:  Things change rapidly in this kind of environment. Make sure you reforecast, especially cash flows and cash, monthly when you close the books.

Don’t Stop Thinking About Tomorrow:  If you have a real business, you need to be it for the long haul. Keep pursuing opportunities. Keep investing in the future. Don’t pare back your vision and ambitions. Just make more conservative investments, insist on shorter payback windows, and adjust expectations about timeframes.

Leadership Counts:  Your people are nervous. They’re concerned about their own bank accounts. Their jobs. Be even more present, more transparent, and more communicative. And set the right tone on expenses with your own decisions. The troops need to know that you care about them — and that the big boss has a steady hand on the wheel.

Doing Well by Doing Good, Part IV

This series of posts has mostly been about things that people or companies do that help make the world a better place — sometimes when it’s their core mission, other times (here and here) when it becomes an important supporting role at the company.

Today’s post is different — it’s actually a Book Short as well of a new book that’s coming out later this fall called Green to Gold:  How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage, published by Yale Press and written by Daniel Esty (a Yale professor and consultant), and a good friend of mine, Andrew Winston, a corporate sustainability consultant.

Green to Gold is a must-read for anyone who (a) holds a leadership position in business or is a business influencer, and (b) cares about the environment we live in.  Its subtitle really best describes the book, which is probably the first (or if not, certainly the best) documentation of successful corporate environmentalstrategy on the market.

It’s a little reminiscent to me of Collins Built to Last and Good to Great in that it is meticulously researched with a mix of company interviews/cooperation and empirical and investigative work.  It doesn’t have Collins “pairing” framework, but it doesn’t need to in order to make its point.

If you liked Al Gore’s movie, An Inconvenient Truth, this book will satisfy your thirst for information about what the heck the corporate world is doing or more important, can do, to do its part in not destroying our ecosystem.  If you didn’t like Gore’s movie or didn’t see it because you don’t like Al Gore or don’t think that many elements of the environmental movement are worthwhile, this book is an even more important read, as it brings the theoretical and scientific to the practical and treats sustainability as the corporate world must treat it in order to adopt it as a mainstream practice — as a driver of capitalistic profit and competitive advantage.

This is a really important work in terms of advancing the cause of corporate social responsibility as it applies to the environment.  Most important, it proves the axiom here that you can, in fact, Do Well by Doing Good.  If you’re interested, you can pre-order the book here.  Also, the authors are writing a companion blog which you can get to here.

Help Me, Help You, Part II

Thanks to the nearly 100 readers who responded to my reader survey this past week.  While I’m not sure it’s a truly statistically significant base of OnlyOnce’s audience (I’ll have to ask my friends over at Authentic Response), I’ll treat it like it is.  Here’s what I learned.  First, the general results:

• Satisfaction levels are good – 46% are regular readers and love it, 48% read occasionally and think it’s ok, and only 6% gave it an “eh – wouldn’t miss it if it went away”
• Entrepreneurship is the most popular topic, with 86% interest, and Leadership/Management is a close second at 82%.  Online/Email Marketing came in at 61% and Book Reviews at 43%.  Current Affairs and Travel (which I almost never use) were 31% and 25%, respectively
• 72% of people feel frequency at 1-2 posts a week is on target.  Only 4.5% want fewer posts, and 24% (those kind souls) want it more often
• Most people other than Return Path staff found the site through a link on another blog rather than search

Next, the open-ended comments were interesting.  A summary snapshot:

• Positive comments were generally about tone and candid approach, succinct posts, and topics.  One nice person noted his/her favorite thing was “the author” (thank you Mom/Dad/Grandma/Mariquita/Michael)
• Constructive comments varied.  Some good ones are noted below:
• “assumes a level of knowledge not everyone has”
• “too heralding of the VC view of the world”
• “too much focus on email/marketing,” “too local/American” (that’s who I am, though)
• “ I would like to see more about what it takes to be a CEO in day to day operations. what skills do you find you need, what obstacles do you come across, issues with driving a company.”
• “A little too much PRish in regards to Return Path”
• “It seems like everything you write about is too positive. Or at least a negative story with a happy ending. Nothing about what sucks to run a company. I run one and a lot of it does suck.”
• “Not enough personal stuff — who is the author?” (see the About Me link on the blog)
  
• “The word vigilante is bandied around way too much by the author”
• And of course someone noted as constructive feedback that I haven’t yet mentioned my mother’s name (sorry, Mom/Joyce!).  And one person suggested I shave.  Thanks, really.

Finally, the demographics of my audience:

• 3 % are under 24, 45% are 25-34, 41% are 35-49, 11% are over 49
• 80% male and 20% female (surprising)
• Company data wasn’t so interesting, or I phrased the question poorly – but one takeaway is that about 1/2 of readers seem to be “in the industry” generally speaking, with lots of Return Path staff subscribing as well as lots of other entrepreneurs and a handful of VCs
• Level/title was more interesting – nearly half the audience is SVP-level or above at their company

Thanks again, everyone, and I’ll take note of this feedback for future postings!

Book Short:  Virtuous Cycle

Danny Meyer’s Setting the Table: The Transforming Power of Hospitality in Business is a fun read if you’re a New Yorker who eats out a lot; a good read for entrepreneurs around scaling leadership skills as the business grows; and a great read for anyone who runs a serious customer service-oriented organization.  I’ve eaten at all of his restaurants multiple times over the years except for the new ones at MOMA (perhaps a few too many times at the Shake Shack), and while I like some more than others (perhaps the Shake Shack a bit too much), they all do have great hospitality as a common theme.

While there are a lot of good lessons in the book, Meyer talks about something he calls the Virtuous Cycle of Enlightened Hospitality that matches the general hierarchy of constituents or stakeholders in a business that I refer to at Return Path:   employees, customers, community, suppliers, investors.  His general point is that if you have happy employees, they make for happy customers, and returns for investors will follow.  While the specifics may or not be true of all businesses, I bet the first and last item are — especially for service-oriented businesses in any industry.  I wish we had a better handle on the Community aspect at Return Path, but we at least do an OK job at it, especially given the geographic diversity within the company.

(Note this was one of Fred’s favorite parts of the book as well from his review — nice to see a professional investor in agreement!)

Book Short:  Crazy Eights

In honor of Return Path being in the midst of its eighth year, I recently read a pair of books with 8 in the title (ok, I would have read them anyway, but that made for a convenient criterion when selecting out of my very large “to read” pile).

Ram Charan’s latest, Know-How:  The 8 Skills That Separate People People Who Perform From Those Who Don’t, was pretty good and classic Charan.  Quick, easy to skim and still get the main points.  The book lost a little credibility with me when Charan lionized Verizon (perhaps he uses a different carrier himself) and Bob Nardelli (the book was published before Nardelli’s high profile dismissal), but makes good points nonetheless.  Some of the 8 Skills he talks about are what you’d expect on the soft side of leadership — building the team, understanding the social system, judging people — but his best examples were particularly actionable around positioning, goal setting, and setting priorities.  The book reminded me much more of Execution and much less of Confronting Reality (which is a good thing).

For years I’ve felt like the last person around to still not have read The 7 Habits of Highly Effective People, so I thought I’d skip straight to the punchline and read Stephen Covey’s newer book, The 8th Habit:  From Effectiveness to Greatness.  Fortunately, as I’d hoped, the new book summarizes the prior book several times over, so if you haven’t read the first, you could certainly just start with this one.  The book also comes with a DVD of 16 short films, some of which are great — both inspirational and poignant.  Unlike most business books, the 8th Habit is NOT skimmable.  It almost has too much material in it and could probably be read multiple times or at least in smaller pieces.  The actual 8th habit Covey talks about is what he calls Find Your Voice and Help Others Find Their Voices and is a great encapsulation of what leading a knowledge worker business is all about.  But the book is much deeper and richer than that in its many models and frameworks and examples/tie-ins to business and goes beyond the “touchy feely” into hard-nosed topics around execution and strategy.

Now I’m looking for the DVD of the first season of Eight is Enough!