This is a topic we write about obsessively in Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams — in fact, it’s basically the whole point of the book! I’ll write some more specific posts here in the coming weeks that take some excerpts from the book, but Bolster is putting on three free and open webinars we’re calling our “Bolster-up Series” over the coming weeks that I want to share with everyone who reads StartupCEO.com.

In this series, I’ll be doing short interviews with CEOs who we work with at Bolster on the different aspects of scaling specific functions, how they diagnosed those problems, and how they leveraged on-demand executive talent to solve those problems. The three events are:

• 7/20 2:00-2:30pm EST: Signs your Finance function isn’t scaling and what to do about it with MediaWallah founder and CEO Nancy Marzouk.
• 8/12 2:00-2:30pm EST: Signs your Revenue function isn’t scaling and what to do about it with Ozcode CEO Shimon Hason.
• 9/15 2:00-2:30pm EST: Signs your Marketing function isn’t scaling and what to do about it with Drip CEO John Tedesco.

You can sign up for the first one on Finance by clicking here.

Best CEO/Entrepreneur Quote Ever, By a Mile

I’ve seen and heard a lot of these.  But perhaps it’s fitting that on Independence Day, I realized that this gem of a quote, not specifically about entrepreneurs or CEOs but very applicable to them, comes from President Theodore Roosevelt in his “Citizenship in a Republic” speech at the Sorbonne in Paris, April 23, 1910:

It is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself for a worthy cause; who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who knew neither victory nor defeat.

Amen, Brother Teddy.  This quote is so good that it appears twice independently (once from me, once in a contributor’s sidebar) in my almost-ready-to-pre-order book, Startup CEO.  In fact, let me quietly take this opportunity to start a bit of a hashtag movement around the topic at #startupceo.  More to come on this next week!

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.

What a View, Part III

We are in the middle of our not-quite-annual senior team 360 review process this week at Return Path.  It’s particularly grueling for me and Angela, our SVP of People, to sit in, facilitate, and participate in 15 of them in such a short period of time, but boy is it worth it!  I’ve written about this process before — here are two of the main posts (overall process, process for my review in particular, and a later year’s update on a process change and unintended consequences of that process change). I’ve also posted my development plans publicly, which I’ll do next month when I finalize it.

This year, I’ve noticed two consistent themes in my direct reports’ review sessions (we do the live 360 format for any VP, not just people who report directly to me), which I think both speak very well of our team overall, and the culture we have here at Return Path.

First, almost every review of an executive had multiple people saying the phrase, “Person X is not your typical head of X department, she really is as much of a general business person and great business partner and leader as she is a great head of X.”  To me, that’s the hallmark of a great executive team.  You want people who are functional experts, but you also need to field the best overall team and a team that puts the business first with understandings of people, the market, internal dependencies, and the broader implications of any and all decisions.  Go Team!

Second, almost every review featured one or more of my staff member’s direct reports saying something like “Maybe this should be in my own development plan, but…”  This mentality of “It’s not you, it’s me,” or in the language of Jim Collins, looking into the mirror and not out the window to solve a problem, is a great part of any company’s operating system.  Love that as well.

Ok.  Ten down, five to go.  Off to the next one…

(This post was written by my colleague Bethany Crystal and originally published on the Bolster blog yesterday. While I am still trying to figure out what posts to put on this blog vs. Bolster’s blog since the blogs are pretty similar, I will occasionally run something in both places.)

At Bolster, we believe that 2021 will mark the rise of the on-demand economy for executives. More than ever before, executives are seeking out roles that distinctly aren’t full-time for a variety of reasons – they’re in between full-time roles and want to stay engaged and meet a wide range of potential employers; they’re retired or semi-retired/post-exit and want to keep working, just not full-time; they’re fully employed but are looking for advisory opportunities to help others; or they are committed to the more flexible lifestyle that being an on-demand affords. As business leaders, you might be wondering how to take advantage of this trend and incorporate on-demand talent onto your existing team. Don’t worry – we’ve got you covered.

Let’s start with a quick primer on the distinct types of on-demand talent. Here are the four most common themes we see among our member network at Bolster:

The Four Types of On-Demand Talent

1. Interim: Someone who is partially or fully dedicated to working with your company, but only temporarily (you can think of them as “filling a gap”)
2. Fractional: Someone who works part-time (or “fractionally”) with your company on an ongoing basis (they “own” the function on a long-term, part-time basis)
3. Advisor or Coach: Someone who supports your existing team by offering external advising, coaching, or mentorship as needed (this might be on a temporary or long-term basis)
4. Project-Based: Someone who is brought on to complete a specific project or a fixed span of work (this is the closest to typical consulting work)

Depending on your business needs, the capacity of your existing team, and your resourcing, you might find it useful to have one or more on-demand executives in the mix at any given time. We’ve also found this can be a great way to keep things fresh at the leadership level and make sure new ideas are circulated with some regularity.

Business Opportunities for On-Demand Talent

While every company’s on-demand talent needs will vary, we’ve already seen a few patterns emerge from the 2,000 executives in our member network. Here are a few times to think about bringing on-demand work to your business.

Choose interim work if you need…

• A temporarily placeholder at the exec level
  Whether unexpected or planned, transitions at the executive level can come with a high cost: Any week that goes by with an unfilled seat adds more work to the team, contributes to business lag, or both. While full executive searches can take six months (or more!) to get right, many CEOs find it helpful to bring on interim help as a “stopgap” in the meantime. The most obvious benefit of interim on-demand work is to prevent your business from falling behind in areas where you may not have a deep bench below the executive level. And you might also consider that bringing in a seasoned professional as you conduct your full-time search will give your team a proxy to compare against, making that placement process a bit easier. Last – while it’s not a guarantee, there’s always the chance that your interim hire is a great fit for you and wants to stick around for the long term! You then benefit from an on-the-job “interview” or audition.
• Surge capacity staffing
  Imagine a situation where your business doesn’t need an executive in a particular function. You’re small, scrappy, and you’re getting along perfectly well with the team you have in place – and you can fill in the bits of executive leadership required for that function yourself from time to time. But then something pops up where you need to be the CEO and can’t afford to ALSO be the CXO. An interim CXO could be the right solution. For example, the 3-5 months run-up to a Series A or B financing could be a good time to bring on an experienced CFO if your only relevant team members are handling AP, AR, and Payroll. Or you could be working on your company’s public launch with a less experienced marketing team and an agency – and an interim CMO could make all the difference between success and sideways.
• Parental leave coverage
  With a growing business trend of increased parental leave coverage, CEOs are starting to use interim executives to fill holes that might temporarily exist on the leadership team. Interim work is particularly useful if there isn’t an obvious “second in command” role on that team who might take on a stretch project in their absence. Implemented correctly, bringing on an interim exec can also help to squash any fears of “getting replaced” while someone is away on leave. As an added bonus, bringing in a new face (if only temporarily) can give the remaining team a chance to “try out” a new leadership style and share feedback about what worked and didn’t work during the interim period.

Choose fractional work if you need…

• A seasoned professional’s experience and skillset (but not all the time)
  Before every full-time leadership hire, there is the sticky “in between” period of need. That’s the period when some work starts piling up, but not quite enough to fill an entire work week for one person at the executive level – or the period when you know you need a more seasoned leader in a function but just can’t afford one full-time. If you don’t have an experienced executive in the role, you miss opportunities for effectively setting up scalable practices and processes. Often, a lack of senior focus in a functional area means that you miss strategic opportunities, and sometimes it also means that you expose yourself to risk that could be avoided with the right person having ownership of the function. This is the perfect time to introduce fractional work to your business. The most classic example of fractional executive talent is the CFO who oversees the bookkeeping and accounting for several companies at once. But you can find a fractional executive for just about anything. You might consider this type of on-demand executive if you don’t yet have anyone in that functional area, if you have a team of less experienced specialists or even a more junior generalist leader in that functional area, if you want a taste of what it’d be like to dedicate more resources there, or if you need just a few things done right, without having to think about them yourself.

Choose advisory or coaching work if you need…

• Mentorship for your current executives
  Sometimes it’s helpful to see what “great” looks like in order to achieve greatness yourself. If you’re looking for a way to give a current leader an added boost to their development plan, consider bringing on someone who can serve as a mentor or advisor on a temporary or long-term basis. Someone who has been in your shoes before and can give advice and guidance based on their experience. This on-demand exec role has two big benefits: The first being that it demonstrates to your executive team that you’re committed to their ongoing success and growth, which boosts morale (and hopefully performance). The second is that you’ll be able to equip your current team with the tools they each need to scale instead of having to bring on a new wave of executives for each business stage. The advisor or coach usually works a few hours per month, once they’ve set up a strong coaching relationship.
• Access to top talent without the full-time price tag
  Just as remote work unlocked the potential to find “the best of the best” without geographic constraints, on-demand work does the same at the executive level. More and more, we’re seeing CEOs incorporate advisors to their business as a way to gain exposure to best in class talent (at a fraction of the cost). This can be a great way to introduce subject matter or functional expertise into your organization without committing to a full-time salary.

Choose project work if you need…

• A fixed-scope expert engagement at the executive level
  Just as tools like Task Rabbit made it possible to find experts to accomplish tasks on a personal level (such as moving furniture or painting a bedroom), on-demand talent makes it possible to find seasoned executives to complete one-off projects at an expert level. That’s why, on Bolster, we ask each each member to indicate what roles they can take on, and also what projects they can be hired to do. As a CEO, you might consider outsourcing some of the crunchy stuff at the exec level that might take a lot of time, or in cases where you need a quick turnaround to get to an MVP. Common projects we’ve seen to date include building sales commission plan structures, designing a go-to-market launch plan for a new product, running due diligence on an acquisition, overhauling pricing and packaging, working on a strategic plan, TAM analysis, budgeting process, or creating a diversity & inclusion strategy for the company.
• An experimental project that won’t distract the current team
  One final area where you might consider on-demand work is for a project that feels more like an addendum to your current business, or an early experiment. At Bolster, we brought on an on-demand executive to help us think through and roll out a brand new product that we’re in the early days of testing right now. We’ve seen other CEOs use project-based work at the exec level for things like evaluating market expansion possibilities or speccing out the MVP of a potential new product.

This is just a short list of some of the possibilities where on-demand talent might support you in your business today. One of our favorite parts about this type of work is just that – the flexibility it offers to you and your team. Whether your business is just getting started or if you’re operating on all cylinders, don’t forget to consider on-demand work as part of your CEO toolkit for this year and beyond.

– Bethany Crystal, February 2, 2021

Gmail as Competition – Another View?

This week, while many from the industry have been in Brussels at the outstanding yet oddly-named MAAWG conference for ISPs and filtering companies, internet marketing pundit Ken Magill had a scary, scary headline related to Google’s insertion of ads in email — Is Gmail Feeding Your Customers to the Competition?

The assertion is that Gmail’s contextual ad program, combined with image blocking in commercial emails, could easily lead to a situation where one of your subscribers doesn’t see your own content but then sees an ad for a competitor in the sidebar.

Scary, I admit, but how much is that really happening?

We analyzed some data from our Postmaster Direct business that is quite revealing, but in a completely counter-intuitive way.

The overall response rate for our mailings sent out in May across all clients, all campaigns, and all ISPs/domains was just under 2%.  The response rate for our mailings in May to Gmail users, on the other hand, was about 3.5%, a whopping 75% BETTER.

Even more stunning is the comparison of response rates in the same time period for subscribers who have joined Postmaster Direct in the last 6 months.  That’s probably a more useful analysis, since the number of Gmail subscribers has grown steadily over time.  On that basis, our overall response rate for May mailings, again across all clients, campaigns, and ISPs/domains, is just over 2.8%.  Howerver, for mailings in May to Gmail users, average response rates were about 5.6%, or 100% BETTER.

I’m not sure what to make of this.  My theory about this at the moment is that Gmail users are generally more sophisticated and therefore are better about keeping their inbox clean and only full of solicited offers, so therefore the user base is more responsive.  But who knows?  What I do make of it is that the issue Ken raises probably isn’t having a big impact on advertisers — or if it is, then Gmail users must be EVEN MORE responsive relative to the rest of the world.

Thanks to Ed Taussig, our director of software development for our list and data group, for this analysis.  Ed is also co-author of our corporate blog’s posting about subject line character length optimization, also a must-read for online marketers if you haven’t seen it.

New Del.icio.us for: Tag

As usual the laggard behind Fred and Brad, I just set up a for:mattblumberg tag on del.icio.us.  Feel free to tag away for me!  If you don’t know what this means, you can read either of their postings about it here or here.

Who Controls the Future of Technology?

I read an interesting article in the Wall Street Journal today, then got to my inbox to find both it and its opposite forwarded to me by Brad.

The Journal says that the consumerization of technology wins out in the end, and that:

In the past, CIOs and their staff had a reputation for being snarky, geeky guys who were always looking for ways to tell employees what they couldn’t do. Now, at the most progressive companies, the tech department’s main job isn’t to say no. Instead, it’s to find a way to let employees safely run any device or program they like. The thinking goes like this: Employees are most productive when they’re allowed to work with the tools that make them happy.

The Times says that it’s all about the CIO when talking about Oracle:

Oracle needs global exposure, and Mr. Hurd needs people who will testify to other big buyers on his behalf…Oracle became big in its 36 years thanks to one of the strongest sales cultures in technology. You can find so many of its former sales executives throughout the industry that sometimes is seems like the Valley’s finishing school for deals. And whatever the business, sales still is all about relationships.

So which is right?  It’s hard to imagine that the sentiment in the Journal piece doesn’t win out in the end or at least that the truth lies somewhere in the middle.  Yes, there are still big enterprise software and hardware deals all over the place, and there probably always will be.  But even the biggest and most complex applications like databases are subject to disruption from below, freemium business models, and open source products.  Courting users, not just people who control budgets (perhaps both), is what a contemporary enterprise software salesforce has to focus on.

Feedburner…They’re Real AND They’re Spectacular

Sometime in early 2004, I met Dick Costolo, the CEO of Feedburner.   We met about at the same time he also met Fred and Brad (I can’t remember who met who first), both of whom subsequently invested in the company.  We hit it off and had a number of informal and formal conversations over the past two and a half years about online media, the interplay of RSS and email and blogs, and entrepreneurship.  Feedburner and Return Path have developed a still-somewhat nascent partnership as well to bring ads in feeds and ads on blogs to Return Path’s Postmaster advertisers.

I was recently fortunate enough to be invited by Dick and his team to join Feedburner’s Board of Directors.  You can read the official note (as official as Feedburner gets!) on Feedburner’s blog here.  I am huge Feedburner fan and am jazzed to be part of their extended team.  The company is impressively leading its market of RSS publisher services and RSS advertising.  It’s all very reminiscent of the early days of email, and the early days of banner advertising before that.  More than that, though, I’ve been incredibly impressed with how the company operates.  They execute swiftly and flawlessly, they have a ton of fun doing it, and they have a very authentic voice and ethos for communicating with and handling their customers that I admire tremendously.  Very Cluetrain Manifesto.

In a much earlier posting, I wrote that entrepreneurs should join other boards as well to get more experience with how different organizations are run and how different board dynamics work, so I guess this means I’m following my own advice.  And so far, it’s all true — I’ve gotten a lot out of the first couple of meetings I’ve attended.  It’s a little weird for me to be the “old media” guy around the table (old meaning web and email, of course), so I’ll have to work hard to not be a Luddite and keep pace with all the new toys.

A Community of Employees

One of the most memorable moments in a valedictorian speech that I’ve heard or read was at my sister-in-law’s graduation from Northwestern about 10 years ago. The speaker’s closing line was something like “Most of all, when you go out into the world, remember to be kind to other people.  It’s one of the best things you can do for the world.”

It’s not as if people are generally trained or predisposed to be UNkind to each other. But respecting other people and being kind to them is sometimes elusive in our busy lives. I think one of the things that makes Return Path more of a community and less of just a “place of work” is this one of our 13 core values:

We are obsessively kind to and respectful of each other

Kindness and respect in the workplace start with the seemingly trivial.  Holding doors open for colleagues, cleaning the coffee machine, helping someone lug a big jug of water and lift it onto the dispenser, and saying a simple “thank you” or “well done” here and there are all acts of kindness and respect. These might seem trivial, but don’t discount the trivial in life.  Being vigilant about the small things sets the right tone for the big things, sort of like the “broken windows” theory of policing says about crime. An atmosphere where people seek out opportunities to help with things like the coffee machine is likely an atmosphere where people seek out opportunities to collaborate on solving problems or cover for a vacationing colleague.

The small things lead to the big things.  We take fit incredibly seriously here.  Fit doesn’t mean that we all have to be the same type of person, or that we all have to like the same kinds of food.  But it means that you have to be kind.  You can be totally frank and direct and challenge authority (more about that in a future post) and still be kind and respectful.  Being a Bull in a China Shop doesn’t work here.

And that’s the difference between a pace to work and a community.

The Fear/Greed Continuum

My old boss from a prior job used to say that every buyer (perhaps every human in general) could be placed at any point in time somewhere on the “fear/greed continuum” of motivation, meaning that you could win him or her over by appealing to the appropriate mix of those two driving forces if you could only figure out where the person sat on the spectrum.  I’ve found this to be true in life, more in selling situations than anything else, but probably in any negotiation.

Think about some examples:

• Is your product an ROI sale (you’re appealing to greed), or do all your prospect’s larger competitors use you (fear they’ll get fired if they don’t adopt)?
• Does the prospective employee really need the new job (e.g., she is motivated by fear), or is she happy where she is but able to be lured away (more motivated by greed) and therefore likely to be swayed by a comp package?
• You’re selling your company – is the buyer excited about accretive financial synergies (greed) or is he motivated because he has a hole in his product line (fear)?

As I read over this post, I guess this is another way of saying “offense vs. defense,” (related to another post I wrote last year) but somehow I find this language more concrete in selling situations.  I don’t think it’s ever the case that any point on the spectrum is more lucrative than any other point (though I suppose extreme fear OR extreme greed might be more lucrative than equal doses of the two) – the point is to use questions and conversation to discover where your target or prospect sits on the spectrum, then tailor your approach accordingly.