Blog on for Swerdloff

My colleague Craig Swerdloff, who runs our Postmaster Network lead generation business and is one of the smartest people in the online advertising business, has started blogging.  Of particular note is this post, in which he talks about the concept of explicit vs. implicit consent in advertising.

His thinking is a lot like some of the things I’ve written about in the past, like the New Media Deal and the We Media Deal.  The bottom line is that advertising has to be valuable and relevant for end users — and properly/carefully delivered.  Welcome to the blogosphere, Craig!

There’s been a growing cry for tech companies to add diversity to their leadership teams and boards, and for good reason. Those two groups are the most influential decision making bodies inside companies, and it’s been well documented that diverse teams, however you define diversity — diversity of demographics, thoughts, professional experience, lived experience — make better decisions. 

Gender, racial, and ethnic representation in executive teams and in board rooms are not new topics.  There’s been a steady drumbeat of them over the last decade, punctuated by some big newsworthy moments like the revelations about Harvey Weinstein and the tragic murder of George Floyd.  

It’s also true that in people-focused organizations, and most tech companies claim to be just that, it’s beneficial to have different types of leaders in terms of role modeling and visibility across the company. As one younger woman on my team years ago said, “if you can see it…you can be it!”

My company Bolster is a platform for CEOs to efficiently build out their executive teams and boards. But while nearly every search starts with a diversity requirement, many don’t end that way. 

Here’s why, and here’s what can be done about it. 

For boards, the “why” is straightforward. Board searches are almost never a priority for CEOs. They’re viewed as optional. Bolster’s Board Benchmark study in 2021 indicated that only a third of private companies have independent directors at all;even later stage private companies only have independent directors two-thirds of the time. That same study indicated that 80% of companies had open Board seats. The comparable longitudinal study in 2022 indicated that the overwhelming majority of those open board seats were still open. 

Independent directors are usually the key to diversity, as the overwhelming majority of founders and VCs are still white and male. It takes a lot of time and effort to recruit and hire and onboard new directors, and in the world of important versus urgent, it will always be merely important. Without prioritizing hiring independents, board diversity may be a lofty goal, but it’s also an empty promise. I wrote about my Rule of 1s here and in Startup Boards – I wish more CEOs and VCs took the practice of independent boards and board diversity seriously. The silver lining here is that when CEOs do end up prioritizing a search for an independent director, they are increasingly open to diverse directors, even if those people have less experience than they might want. That openness to directors who may never have been on a corporate board (but who are board-ready), who may be a CXO instead of a CEO, is key. Of the several dozen independent directors Bolster has helped match to companies in the past year, almost 70% of them are from demographic populations that are historically underrepresented in the boardroom.

Diversity is stalling for Senior Executive hiring for the opposite reason. Exec hires are usually urgent enough that CEOs prioritize them. And they frequently start their searches by talking about the importance of diversity. But Senior Executives are much more often hired for their resume than for competency or potential. Almost all executive searches start with some variation of this line, which I’m lifting directly from a prior post: “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to be hired. They have made a ton of money, and they have moved beyond that job in their career progression. So inevitably, the search moves on to look for the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people may or may not be easy to find or available, but they feel less risky. In the somewhat insular world of tech, those candidates are also far less likely to be diverse in background, experience, thought, or, yes, demographics.

Running a comprehensive executive search based on competencies, cultural fit, scale experience, and general industry or analogous industry experience is much harder. It takes time, patience, digging deeper to surface overlooked candidates or to check references, and probably a little more risk taking on the part of CEOs. And while CEOs may be willing to take some risk on a first-time independent director, fewer are willing to take a comparable level of risk on an unproven or less known executive hire. 

For some CEOs, the answer is just to take more risk — or more to the point, recognize that any senior hire carries risk along a number of dimensions, so there’s no reason to prioritize your narrow view of resume pedigree over any critical vector. For others, the answer may be to bring the focus of diversity in senior hires to “second level” leaders like Managers, Directors, or VPs, where the perceived risk is lower, and the willingness to invest in training and mentorship is higher. Those people in turn can be promoted over time into more senior positions. 

Not every executive or board hire has to be demographically diverse. Not every executive team or board has to have individual quotas for different identity groups, and diversity has many flavors to it. But without doing the work, tech CEOs will continue to bemoan the lack of diversity in their leadership ranks, and miss out on the benefits of diverse leadership, while not taking ownership for those efforts stalling.

Pivot, Don’t Jump!

I spoke last night at the NYC Lean Startup Meetup, which was fun.  I will write a couple other posts based on the experience over the next week or so.  The Meetup is all about creating “lean startups,” not just meaning lean as in cheap and lightweight, but meaning smart at doing product development from the perspective of finding the quickest path to product-market fit.  No wasted cycles of innovation.  Something we are spending a lot of time on right now at Return Path, actually.

My topic was “The Pivot,” by which the group meant How do you change your product idea/formation quickly and nimbly when you discover that your prior conception of “product-market fit” is off?  I talked a bit about the pivots we’ve done over the years here, not just the corporate ones, but some of the essential product ones as well.  One of the comments a member of the Meetup made that really stuck with me was that you have to “Pivot, Don’t Jump” when making changes to your business or product.

This has been true of Return Path’s pivots over the years.  Our pivots have all had two very solid foundation points — the company’s deep expertise in email, and our customer base.  Every pivot we’ve done has been in some way at the request/urging of our clients, and the new directions have always been in line with our core capabilities.  While we have a talented team that probably could execute lots of different businesses well, it’s hard to see us being successful in other areas that are farther afield.

People over the years, for example, have suggested that we should get into SMS deliverability — isn’t that going to be a hot topic?  We don’t know.  We don’t spend our lives immersed in text messaging.  What about getting into measurement of social media messaging — isn’t that related?  Maybe, but it’s not in our wheelhouse.  Expanding from email deliverability software and analytics, into services, into data, into whitelisting on the other hand – those were pivots, not jumps.

One other note of course, is that the larger your business is, and the more investors have a stake in it, the harder it is to make BIG pivots or any kind of jumps.  Innovation is still critical, but innovating from a well-protected core is what it’s all about, not chasing new shiny objects.

I help mentor CEOs on executive hiring all the time. One common refrain I hear when we’re talking about requirements for the job is about something I like to call The Mythical Playbook. If I only had the exec with the right playbook, thinks the hiring CEO, all my problems in that executive’s area would be magically solved.

I once hired a senior executive with that same mentality. They had the pedigree. They had taken a similar SaaS company in an adjacent space from $50mm to $250mm in revenue in a sub-group within their functional area. They had killer references who said they were ready to graduate to the C-level job. They had The Playbook! 

Suffice to say, things did not go as planned. I ignored an early sign of trouble, at my own peril. The exec came to me with a new org chart for the department, one with 45 people on it instead of the 20-25 who were currently there. I believed the department was understaffed but was surprised to see the magnitude of the ask. When I pushed back in general, the response I got was “I plan to overspend and overdeliver.” Hmm, ok. I don’t mind that, although a more detailed plan might be useful.  

Then I pushed back on a specific hire, pointing to a box in the org chart with a title that didn’t make sense to me. The response I got was “Yeah, I’m not entirely sure what that person does either, but I know I need that, trust me.” Yikes. 

There are two reasons why The Playbook is mythical. 

The first reason there’s no such thing as a Playbook for executives is that every situation is different. No two companies are identical in terms of offering or culture or structure. Even within the same industry, no two competitive landscapes are the same at different points in time. If life as a senior executive were as simple as following a Playbook, people would make a zillion dollars off publishing Playbooks, and senior executive jobs would be easier to do, and no one would get fired from them.

Now, I’m not saying there isn’t value in analogous experience. There is! But when hiring an executive, you’re not solely looking for someone who claims to know all the answers based on previous experience. That is a recipe for blindly following a pattern that might or might not exist. The value in the analogous experience is in knowing what things worked, sure, but more importantly in knowing when they worked, why they worked, under what conditions they worked, what alternatives were considered, and what things fell apart on the road to success. A Playbook is only useful if it can be applied thoughtfully and flexibly to new situations.

The second reason there’s no such thing as a Playbook when it comes to hiring executives is that the person who might have written the Playbook is actually not available for your job. Most CEOs start a search by saying, “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to you. They have made a ton of money, and they have moved beyond your job in their career progression. What you want is the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people are much harder to find. And when you find them, they don’t have the Playbook. They may have seen a couple chapters of it, but that’s about all.

In the end, the department I referenced above was more successful, but not because of adherence to the new exec’s entire Playbook. The Playbook got the department out over its skis – we overspent, but we did not overdeliver. The new exec ended up leaving the company before they could implement a lot, and that person’s successor ended up refocusing and rightsizing the department. That said, the best thing the department got out of the exec with the Playbook was their successor, which was huge — one element of a strong exec’s Playbook is how to build a machine as opposed to just playing whack-a-mole and solving problems haphazardly.

(Note – I am using the singular they in this and in other posts now, as Brad. Mahendra, and I chose to do in Startup Boards. I don’t love it, but it seems to be becoming the standard for gender neutral writing, plus it helps mask identities as well when I write posts like this.)

I’m fascinated with this topic and how it’s evolving in society. In Part I, a couple years ago now, I changed my long-held point of view from “CEOs should only wade into politics when there’s a direct impact on their business” (things like taxes and specific regulations, legal immigration) — to believing that CEOs can/should wade into politics when there’s an indirect impact on business. In that post, I defined my new line/scope as being one that includes the health and functioning of our democracy, which you can tie to business interests in so many ways, not the least of which this week is the Fitch downgrade of the US credit rating over governance concerns. Other CEOs will have other definitions of indirect, and obviously that’s ok. No judgment here!

I am a regular viewer of Meet the Press on Monday mornings in the gym on DVR. Have been for years. This weekend, Chuck Todd’s “Data Download” segment was all about this topic. The data he presented is really interesting:

58% of people think it’s inappropriate for companies to take stands on issues. The best that gets by party is that Democrats are slightly more inclined to think it’s appropriate for companies to take stands on issues (47/43), but for Republicans and Independents, it’s a losing issue by a wide margin.

To that end, consumers are likely to punish companies who DO take stands on issues, by an overall margin of 47/24 (not sure where everyone else is). The “more likely” applies to people of all political persuasions.

These last two tables of his are interesting. Lower income people feel like it’s inappropriate for companies to take stands on issues more than higher earners, but all income levels have an unfavorable view, and…

…older people are also more likely to have an unfavorable view of companies who wade into politics than younger people, but again, all ages have an unfavorable view

As I said in Part I of this series, “I still believe that on a number of issues in current events, CEOs face a lose-lose proposition by wading into politics,” risking alienation of customers, employees, and other stakeholders. The data from Meet the Press supports that, at least to some extent. That said, I also acknowledge that the more polarized and less functional the government is…the more of a leadership vacuum there is on issues facing us all.

Feature Requests

Here are two new features I’d like to see in life:

1. Any time you hit “reply to all” when you are in the BCC line – a giant red alert should pop up and say “are you really sure you want to let all these people know that you were BCCd on this thread?”
2. Any time you place a call to a cell phone that’s outside of the person’s normal time zone – a giant red alert should pop up and say “are you sure you want to call this person at 3 a.m. in Singapore?” before completing the call

I’m not sure to whom these requests should be addressed, so I’ll just start with the open web.

Who Are Your CPO and COO?

Every senior management team needs a CPO and a COO.  No, I’m not talking about Privacy and Operations.  I’m talking about Paranoia and Optimism.  On my leadership team at Return Path, many of us are Paranoid and many of us are Optimistic, and many of us can play both roles.  But I’m fortunate to have two business partners who are the Chiefs – George Bilbrey is our Chief Paranoia Officer, and Anita Absey is our Chief Optimism Officer.  Those monikers fit their respective roles (product and sales) as well as their personalities.

My view is simple – both traits are critical to have around the management table, and they’re best when they’re in some kind of equilibrium.  Optimism keeps you running forward in a straight line.  The belief that you can successfully execute on your plan, with a spring in your step and a smile on your face, is very motivating.  Paranoia keeps you looking around corners.  It may also keep you awake at night, but it’s the driving force for seeing potential threats to the business that aren’t necessarily obvious and keeping you on your toes.  I wrote about the benefits and limits of paranoia (with an extreme example) years ago here.

Too much of either trait would be a disaster for a team’s psyche.  But both are critical points of view that need a loud voice in any management discussion.  It’s a little bit like making sure your management team knows its actual and target location along the Fear/Greed Continuum.

Firsts, Still

After more than 13 years in the job, I run into “firsts” less and less often these days.  But in the past week, I’ve had three of them. They’re incredibly different, and it’s awkward to write about them in the same post, but the “firsts” theme holds them together.

One was incredibly tragic — one of our colleagues at Return Path died suddenly and unexpectedly.  Even though we’ve lost two other employees in the last 18 months to cancer, there was something different about this one.  While there’s no good way to die, the suddenness of Joel’s passing was a real shock to me and to the organization, and of course more importantly, to his wife.

The second was that I came face to face with a judge in the state of Delaware for the first time around some litigation we’re in the middle of now.  While I can’t comment on this for obvious reasons, you never think when you decide to incorporate in Delaware that a trip to a courthouse in Wilmington is in your future.

The third, which can only be described as bittersweet, is that we had our first long-time employee retire!  Now THAT’S something you never think about when you run a startup.  But Sophie Miller Audette, one of our first 20 employees going back to 2000 and the sixth longest tenured person at the company today, has decided to retire and move on to other adventures in her already rich life.  A quick search on my blog reveals that I’ve blogged about Sophie three times since I started OnlyOnce 9 years ago (as of next week).  The first time was in 2004 when I quoted her memorable line, “In my next life, I want to come back as a client.”  The second and third times were in 2005 and were about the company’s commitment to helping to find a cure for Multiple Sclerosis, which Sophie was diagnosed with almost 10 years ago now.  Sophie has been an inspiration to many of us for a long time, and while we’ll miss her day-to-day, she’ll always be part of the Return Path family.  Picture of her, me, and Anita at her “retirement dinner” earlier this week below.

I always say that one of the best parts about being in this job for this long is that there are always new challenges and new opportunities to learn and grow.  The last couple weeks, full of firsts, proved the point!

How to Negotiate a Term Sheet with a VC, Part IV

Brad is making  new postings easy this week.  Here’s another good one from the VC’s perspective on liquidation preference.

Clients at Different Levels

Recently, I’ve become more aware that we have a huge range of clients when it comes to the level of the person we interact with at the client organization.  I suppose this has always been true, but it’s struck me much more of late as we’ve really ramped up our client base in the social networking/web 2.0 arena, where most of our clients are CEOs and COOs as opposed to Email Marketing Managers.

Of course, we don’t care who our day-to-day client is, as long as the person is enough of a decision maker and subject matter expert to effectively partner with us, whether it’s on deliverability via Sender Score or on list management or advertising via the Postmaster Network.  There are two main differences I have seen between the levels of client.  I suppose neither one is an earth-shattering revelation in the end, though.

First, the CEO/COO as client tends to be a MUCH MORE ENGAGED and knowledgeable client.  Some of these people know far, far more about the ins and outs of micro details of their businesses (and in the case of deliverability, the micro details of how ISPs filter email) than our average client.  I’d expect this type of client to be in command of the macro details of his or her business, but the level of "in the weeds" knowledge is impressive.  These clients are thirsty for information that goes beyond the scope of our work together.

Second, the CEO/COO as client is MUCH MORE PASSIONATE about his or her business.  It pisses them off when their email doesn’t get delivered.  They care deeply that our Postmaster opt-in might impact their registration rates by 0.5%.  They get very animated in discussions and tend to nod and gesture a lot more than take notes in a notebook.

My main takeaway from this?  If you run a business — how do you make sure your front line people are as fired up as you are?  You may never be able to give people the same kind of macro view you have of the company or the industry (although you can certainly make a good effort at it), but keeping people excited about what they do and igniting their intellectual curiosity on a regular basis will almost certainly lead to more successful outcomes in the details of your company.

Just Because You Can Do Something, Doesn’t Mean You Should

This has always been one of my favorite axioms for life and for entrepreneurship.  Today’s example comes from Brad’s new running blog, and ultimately from an AP story reported in the Northwest Florida Daily News.  The full story is here, but this teaser ought to get you hooked enough to click through, much as drivers slow down to see accidents on the other side of the road:

Pain doesn’t defeat unshod marathoners

Last month, after returning from an eight-mile run, Tsuyoshi Yoshino heated up a three-inch sewing needle until it turned bright red. Then, he says, he plunged the glowing instrument into the ball of his foot, puncturing a three-inch-long blister.

Despite the risk of infection, he walked around his San Diego house for 20 minutes on the open wound to get used to the pain. “It’s not something I like doing,” he says. “But I have to.”

Apologies to the squeamish.  Happy New Year!