A New VC in Town…Sort of

My friend and Board member Fred Wilson just announced last week the formation of his new VC firm, Union Square Ventures, along with his partner Brad Burnham.  Brad Feld beat me to the “way to go” posting, so while I chime in with my congratulations to Fred and Brad and assert to the rest of the VC/tech blogging world that this firm will succeed famously, I thought I’d comment on two other aspects of Union Square Ventures’ formation.

First, NYC has long been a haven for later stage private equity and buy-outs, and there’s a big need in the NYC area (even the DC-Boston corridor more broadly) for top tier early stage venture capital players.  While there are fewer core techonlogy companies in the area, there are an increasing number of application and service companies that are building great businesses in this part of the country, and there are not enough great VCs to keep up.  West coast VCs are often (but not always, as I’ve seen in my investors Brad from Mobius and Greg Sands from Sutter Hill) allergic to east coast deals, and sometimes it’s just good to have one of your main investors walking distance away.  Fred and Brad have the reputations, track records, and networks to at least partially fill this void.

Second, as Fred noted in a subsequent posting on Flatiron and its remaining portfolio companies (including Return Path), Fred and his former partners from JP Morgan are not abandoning their prior investments.  This speaks volumes about the kind of people they are and the commitment they have to their entrepreneurs.

I’m sure Union Square Ventures will be successful, and I’m glad I have the opportunity to see it up close.

Post 3 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO and When it is Time to Hire Your First Chief Financial Officer.)

 A lot of startups have a bookkeeper, accountant, or even a spouse of a founder or employee handle the finances when they first start out, and that’s fine. But at some point you’ll want to hire a CFO and if you’re dealing with a lot of chaos it’s easy to think, “well, anybody is better than what we have now.” But I would hold off on that thinking because the CFO, a great one, will do a lot more than just manage the finances, AP, and AR. A great one can do four things particularly well:

First, a great CFO will spend time learning and steeping themselves in the substance of the business; they’ll understand the product, the people who created it and market it and sell it, and they’ll spend time in-market with customers and partners.  They do not believe their function is only “corporate” or only a service function; instead, they see it as both of those, as strategic, and as pathway to greater financial understanding for every person in the company. They insist that the people in their department do the same.

Second, a great CFO is deliberate about regularly reviewing homemade systems, processes, and spreadsheets and looking for opportunities to streamline things, reinvent them, or move them into systems.  Once most things are automated and in systems, they are constantly evaluating whether or not the systems are serving the business well enough and are looking to integrate systems across the company.  They are not afraid to tear down and reinvent systems and processes that they themselves set up in the past. That is, their ego is less important than doing what’s best for the company.

Third, a great CFO will have the right balance of pessimism and optimism and they are strong at communicating both.  While they are proactive and timely about delivering bad news to you and the Board, their orientation isn’t around “no” and bad news.  Their orientation is around investment and return and always thinking about things going on around them in the company through the lens of realistic opportunity.

They can fly at multiple altitudes at the same time, noticing the smallest detail that’s off while thinking about business models and strategy.  While most executives need to be strategic and tactical at the same time, the CFO needs to be like that more than most — mostly because the details and tactics are frequently life-or-death for your startup.

(Posted on the Bolster blog here).

(This is the second post in the series…….the first one on When to Hire your First Chief Revenue Officer is here.)

If you’re looking for a great CRO, one thing you want to avoid is being “sold” by a dynamic and engaging salesperson instead of finding the best CRO for your company. Over the two-plus decades of working closely with CROs I figured out what “great” looks like and I’ve found that there are five things that great CROs do. While you might not find all these characteristics and attributes in one person, you should definitely look for them!

First, a great CRO knows when to turn up the volume, and when not to.  Thinking through our metaphor/framework for enterprise sales that I wrote about in an earlier post – from Whiteboard to Powerpoint to PDF – great CROs know when they aren’t yet in PDF mode.  In the early days when your organization is selling on Whiteboard or figuring out the transition to Powerpoint, when you’re adding sales reps like crazy, this is not the time to quickly get to the PDF stage even though everyone in your organization will be clamoring for that. Sure, there could be a ton of opportunity to pursue but scaling quickly is inefficient and unlikely to be successful because scaling before the PDF stage still depends on the success of individual hunters.  Only when the organization has made the true transition to PDF can a sales machine scale rapidly, and a great CRO understands this.

Second, a great CRO gives credit to others first when things go well and looks inward first when things go poorly.  This is easier said than done because the tendency for people in any organization is self-preservation and the easiest way to do this is take credit and blame others. But the geat CROs are the first ones to thank their fellow executives in marketing, in product, in finance, for collaboration and successes.  They are also the first ones to thank their team publicly for a good quarter.  When they miss a quarter, the first thing they do is figure out why the Sales team blew it, as opposed to blaming the product or marketing or economy…or even customers themselves.

Third, a great CRO is maniacally focused on building a conveyor belt-style pipeline for sales talent so they don’t lose momentum when a rep quits or gets fired.  Notice that I didn’t say a great CRO was “focused” on building the pipeline or “passionate” about building the pipeline—I used the term “maniacal” because that’s what a great CRO looks like to everyone else in the organization: a crazy, intense, nonstop, extremist who religiously works on their talent pipeline.  “Quota just walked out the door” is never something you’ll hear from a great CRO because that’s not an option in a well-tuned sales machine where multiple layers of reps are consistently trained, managed, and groomed for the next level of selling. 

Fourth, a great CRO will be able to say “no” to overpaying and over-promoting without ruffling feathers on the sales team. An inability to stay disciplined on compensation is the second-worst thing a Sales leader can do and if they get compensation wrong by paying reps too much base or having too much commission in easily-repeatable form, you’ll pay for it—without the producivity gains. Reps who are overpaid get “fat and happy,” when what you want is for them to be “lean and hungry.” The worst thing a CRO can do? The worst thing a CRO can do, and something the great CROs won’t do despite great pressure, is to promote a superstar sales rep with no management aptitude or training into a sales manager role. I’ve seen this play out several times and it doesn’t end well. Either the superstar will not be able to lead and will exit the organization, or the superstar will end up poisoning an entire team and lots of your reps will exit the organization.  Great CROs know how to say no to the misguided request for a promotion and how to keep people engaged without overpaying them.

Fifth, a great CRO deosn’t belive in the “magic rolodex” (yes, I realize that term is a bit dated!). They might have a magic rolodex, deep networks, and personal ties to players in the ecosystem, but unless you are hiring a sales rep who literally just finished selling a competitive solution to the same target customer set, sales reps who claim they come with a built-in book of business can only deliver on that promise 1% of the time.  It’s alluring — but it just doesn’t work out that way.  Great CROs know how to ferret that out and hire instead the reps who will fit in the company culture and work to improve the processes and systems in place.

Hiring a great CRO isn’t easy but hiring the first (or last) person you interview because of their excellent communication skills will be a disaster. Look for a CRO who understands the pacing to scaling, is humble enough to give credit to others and avoid blaming, and who is “maniacal” about the team—coaching and mentoring them, providing the rails so that the team can do their best work.

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

New People Electrify the Organization

We had a good year in 2009, but it was tough.  Whose wasn’t?  Sales were harder to come by, more existing customers left or asked for price relief than usual, and bills were hard to collect.  Worse than that, internally a lot of people were in a funk all year.  Someone on our team started calling it “corporate ennui.”  Even though our business was strong overall and we didn’t do any layoffs or salary cuts, I think people had a hard time looking around them, seeing friends and relatives losing their jobs en masse, and feeling happy and secure.  And as a company, we were doing well and growing the top line, but we froze a lot of new projects and were in a bit of a defensive posture all year.

What a difference a year makes.  This year, still not perfect, is going much better for us.  Business conditions are loosening up, and many of our clients have turned the corner.  Financially, we’re stronger than ever.  And most important, the mood in the company is great.  I think there are a bunch of reasons for that – we’re investing more, we’re doing a ton of new innovation, people have travel budgets again, and people see our clients and their own friends in better financial positions.

But by far, I think the most impactful change to the organizational mood we’re seeing is a direct result of one thing:  hiring.  We are adding a lot of new people this year – probably 60 over the course of the year on top of the 150 we had at the beginning of the year.  And my observation, no matter which office of ours I visit, is that the new people are electrifying the organization.  Part of that is that new people come in fresh and excited (perhaps particularly excited to have a new job in this environment).  Part of it is that new people are often pleasantly surprised by our culture and working environment.  Part of it is that new people come in and add capacity to the team, which enables everyone to work on more new things.  And part of it is that every new person that comes in needs mentoring by the old timers, which gives the existing staff reminders and extra reason to be psyched about what they’re doing, and what the company’s all about.

Whether it’s one of these things or all of them, I’m not sure I care.  I’m just happy the last 18 months are over.  The world is a brighter place, and so is Return Path.  And to all of our new people (recent and future), welcome…thanks for reinvigorating the organization!

Transparency Rules

I think each and every one of our 13 core values at Return Path is important to our culture and to our success.  And I generally don’t rank them.  But if I did, People First is a leading contender to be at the top of the list. The other leading contender would be this last one in the series:

We believe in being transparent and direct

The big Inc. Magazine story about us last year talked a lot about our commitment to transparency and some of the challenges that come with being transparent and direct with people. I’d like to highlight here some of the benefits of being transparent, and the benefits of being direct (sometimes those two things are the same, sometimes they are different).

Transparency’s benefits are so numerous that it’s hard to pick just one or two themes to write about, but my favorite benefit is empowerment.  Especially in a world where information is increasingly available and free, hoarding it comes at a high cost.

• If everyone in the company knows that you’re short of plan and disappointed about that, the majority of people will exercise hawkish judgment about expenses.  The opposite is true as well.  If people know you’re running ahead of plan, they will be more willing to take risks and make investments. Without transparency of financials, people are just more in the dark and looking for all answers and judgment to come from above
• If everyone on your staff understands the process you went through to make a tough call about an element of your strategy, they are not only more likely to understand and support the decision, but they learn from you how to make decisions in the first place
• If your Board knows you’re having a tough quarter from the get go, they’re not surprised at the quarterly meeting and don’t force you to spend painful and precious minutes in the meeting On the firing line reporting on the details. Instead, they can spend time leading up to the meeting thinking about the details of the problems and how they can help or what insights they can bring to bear

Transparency does have some limits, even today.  There are three main limits we run into. One is compensation — still too touchy and wrapped up in people’s self esteem to post on the wall (though I have heard about a couple companies that do that, believe it or not). Another is terminations. Although you might want to tell the company that you fired Sally because she wasn’t carrying her weight, the long term value you derive from dignity and kindness trump any short term value you might derive from such a statement (plus, people know when Sally isn’t carrying her weight, anyway). The third limit to transparency is around half-baked ideas. Although you might sometimes want to try ideas on for size publicly, you have to be careful not to send people scurrying off in the wrong direction just because you blurted something out in a meeting.

The second half of this value statement is about being direct.  Being direct mostly has benefits in terms of efficiency. You can be direct and still be polite and kind.  But being direct means not beating around the bush, being political, or being conflict avoidant.  It means nipping problems in the bud and saving yourself time or money in the long run.

• If you are direct with an employee who is not performing well with data to back it up, the employee has a much better shot at improving than if you delegate the feedback to HR, wait for the next annual performance review, or go passive and skip the feedback entirely
• If you are direct with a boss who you think is treating you unfairly, your odds of fixing the situation go way up
• If there’s bad news to deliver, be direct about it — look the other person in the eye, deliver the news crisply and succinctly, and as quickly as you can after finding it out or deciding on it yourself

Avoid euphemisms at all cost. Telling someone you “might have to rethink things” is not the same as saying “I will have to fire you if xyz don’t happen in the next 30 days.” Saying “xyz would be good for you to do” is not the same as saying “the way for you to get promoted is to consistently do xyz.”

Being transparent and direct are increasingly table stakes for successful companies full of knowledge workers who want to be empowered and clear on where they stand.

I’ve really enjoyed writing all of these values out in living color. I will do a wrap up post shortly.

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around the sale process itself.  There are some interesting things in it — the arc and timeline of a deal, working with and through advisors vs. principals dealing with each other directly, optimizing for different stakeholders, and a wonderful long sidebar by my friends and advisors Brian Andersen and Mark Greenbaum from Luma Partners on how to think strategically about an exit and how buyers think.  It’s probably worth buying the whole book just for that.

But what I want to write about here is coping with a failed deal – something my team and I unfortunately had to do a couple years before we actually sold the company and something I’ve never written about or discussed publicly.

In 2017, we almost sold Return Path.  You hear people talk about that from time to time, and frequently it just means “we had a good offer but decided not to take it.”  But in this case, I meant it.  We had a good offer.  We talked to a couple other potential buyers in the industry and ended up getting a great offer.  From a great buyer.  We decided to pull the trigger.  It was time.  We got through the entire deal process, I mean EVERYTHING.  Diligence was painful, thorough – and completed.  Both sides had signed off on things many times along the way.  Documents were done, lawyers had signed off on them, our Board had signed off on them, they had been posted to DocuSign, and our signatures were in escrow.  The press release was written and scheduled to go out in less than 48 hours.  Our all-hands meeting was scheduled.  The acquirer had already sent us their swag to hand out.  About 80 people out of 400+ employees at the company knew about it.  In the football analogy, we weren’t inside the red zone.  We were on the 1-yard line.  

Then the call came.  “I can’t believe we have to tell you this, but our CEO just decided to pull the plug on this at the last minute.”  Buh.  Bye.  To say this was a disappointment is the understatement of a career.  

That evening, I was staying over at a friend’s apartment in Manhattan while Mariquita and the kids were away at the beach with her parents.  After the call came in, I grabbed the two other execs who were still in the office, and we went immediately to a bar.  That calmed me down a little bit.  Then I wandered through Central Park up to the apartment and spent about 4 hours on the phone in a series of cathartic phone calls with the rest of the executive team, some of my closest friends and advisors, and Board members.  

The next couple of days were awful.  We had to tell a huge number of employees “Uh sorry, just kidding.  You know all those stock options that were just about to turn into cash?  Sorry.  The new company we were all excited to join?  Psych!”  The worst part was scrambling to turn the already-scheduled all-hands meeting to announce the deal into just another quarterly update.  Everyone in the room for that meeting who knew about the failed deal just looked at each other with disbelief. We were still in shock.

Eventually of course, we bounced back.  I am now an even more ardent believer in the expression, “What doesn’t kill you makes you stronger.”  The company ended up recovering from this and doing a number of things to make us even better in the years that followed, leading to our eventual sale.  But I will say, it was just terrible, and nothing about the recovery was easy.  I talk about some of the specific steps we took in the book.  But mostly, I hope no one ever has to go through anything like this again.  This was too big, too close to the end, and too well known.  Our team will have deep scar tissue from it for a long time.

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

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

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

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

Sunday, March 15 – Day -1

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

Monday, March 16, Day 0

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

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

Why I joined the DMA Board, and what you can expect of me in that role

I don’t normally think of myself as a rebel. But one outcome of the DMA’s recent proxy fight with Board member Gerry Pike is that I’ve been appointed to the DMA’s Board and its Executive Committee and have been labeled “part of the reform movement” in the trade press. While I wasn’t actively leading the charge on DMA reform with Gerry, I am very enthusiastic about taking up my new role.

I gave Gerry my proxy and support for a number of reasons, and those reasons will form the basis of my agenda as a DMA Board member. As a DMA member, and one who used to be fairly active, I have grown increasingly frustrated with the DMA over the past few years.

1. The DMA could be stronger in fighting for consumers’ interests. Why? Because what’s good for consumers is great for direct marketers. Marketing is not what it used to be, the lines between good and bad actors have been blurred, and the consumer is now in charge. The DMA needs to more emphatically embrace that and lead change among its membership to do the same. The DMA’s ethics operation seems to work well, but the DMA can’t and shouldn’t become a police state and catch every violation of every member company. Its best practices and guidelines take too long to produce and usually end up too watered down to be meaningful in a world where the organization is promoting industry self-regulation. By aggressively fighting for consumers, the DMA can show the world that a real direct marketer is an honest marketer that consumers want to hear from and buy from.

2. Despite a number of very good ideas, the DMA’s execution around interactive marketing has been lacking. The DMA needs to accept that interactive marketing IS direct marketing – not a subset, not a weird little niche. It’s the heart and soul of the direct marketing industry. It’s our future. The acquisition of the EEC has been one bright spot, but the DMA could do much more to make the EEC more impactful, grow its membership, and replicate it to extend the DMA’s reach into other areas of interactive marketing, from search to display advertising to lead generation. The DMA’s staff still has extremely limited experience in interactive marketing, they haven’t had a thought leader around interactive on staff for several years, and their own interactive marketing efforts are far from best practice. Finally, the DMA’s government affairs group, perhaps its greatest strength, still seems disproportionately focused on direct mail issues. The DMA should maintain its staunch support of traditional direct marketers while investing in the future, making interactive marketing an equal or larger priority than traditional direct marketing. We have to invest in the future.

3. Finally, I think the DMA suffers from a lack of transparency that doesn’t serve it well in the hyper-connected world we live in here in 2009 – that’s a nice way of saying the organization has a big PR problem. The organization does a lot of great work that never gets adequately publicized. This whole proxy fight episode is another example, both in the weak response from the DMA and also in a lot of the complaints Gerry lodged against the organization, many of which the organization says are untrue or misleading. Senior DMA execs or Board members should be blogging. They should be active thought leaders in the community. They should be much more engaged with their members to both understand member needs and requirements and more aggressively promote their agenda.

In short, I will be an independent voice who advocates for progress and change in the areas that I consider to be most important, and I will be transparent and open about expressing my views. I’ve already been clear with the existing DMA Board and management that I do have this agenda, and that I hope the organization will embrace it. If they do, even if only in part, I think it will be to the DMA’s benefit as well as the benefit of its members. If they reject it wholesale, my interest in long-term involvement will be fairly low.

That’s the story. As I said up front, I am taking up this new role with enthusiasm and with the belief that the DMA is open to change and progress. We’ll see how it goes, and I will blog about it as often as I can.

Do you have thoughts on the future of the DMA? I’d love to hear from you. You can leave a comment below or email me directly at matt at returnpath dot net.

Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline

As I mentioned a few weeks ago here, I’m excited to be writing a book called Startup CEO:  A Field Guide to Building and Running Your Company, to be published by Wiley & Sons next summer.  Since many readers of OnlyOnce are my target audience for the book, I thought I’d post my current outline and ask for input and feedback on it.  So here it is, still a bit of a work in progress.  Please comment away and let me know what you think, what’s missing, what’s not interesting!

1           Part One: Vision and Strategy (Defining the Company)
1.1          Setting the Company’s Agenda
1.2          NIHITO! (or, “Nothing Interesting Happens in the Office”)
1.3          Setting the Business Direction
1.4          Strategic Planning, Part I: Turning Concepts Into Strategy
1.5          Strategic Planning, Part II: Creating the Plan
1.6          Defining Mission, Vision and Values
1.7          Communicating Vision and Strategy
1.8          The Role of M&A
1.9          The Art of the Pivot
1.10       How Vision and Strategy Change over Time

2           Part Two: Talent (Building the Company’s Human Capital)
2.1          Building a Team
2.2          Scaling the Team
2.3          Culture
2.4          Interviewing
2.5          Recruiting
2.6          Onboarding
2.7          Setting Goals
2.8          Feedback
2.9          Development
2.10       Compensation
2.11       Promoting
2.12       Rewarding
2.13       Managing Remote Offices and Employees
2.14       Firing: When It’s Not Working
2.15       How Talent Changes over Time

3           Part Three: Execution (Aligning Resources with Strategy)
3.1          Making Sure There’s Enough Money in the Bank
3.2          Types of Financing
3.3          Fundraising Basics
3.4          Negotiating Deals
3.5          Pros and Cons of Outside Financing
3.6          Forecasting and Budgeting
3.7          Creating a Company Operating System
3.8          Meeting Routines
3.9          Driving Alignment
3.10       A Metrics-Driven Approach to Running a Business
3.11       Learning
3.12       Post-Mortems
3.13       Thinking About Exits
3.14       How Execution Changes over Time
3.14.1      Finance
3.14.2      Execution

4           Part Four: Management And Leadership (The How of Being a CEO)
4.1          Leading an Executive Team
4.2          Critical Personal Traits
4.3          Being Collaborative
4.4          Being Decisive: Balancing Authority and Consensus
4.5          The Value of Symbolism
4.6          Getting the Most out of People
4.7          Diving Deep without Being Disruptive
4.8          Articulating Purpose
4.9          Collecting Data from the Organization
4.10       Managing in an Economic Downturn
4.11       Managing in Good Times vs. Bad Times
4.12       Communication
4.12.1      Macro (to Your Company and Customers)
4.12.2      Micro (One-on-One)
4.13       How Management and Leadership Change over Time

5           Part Five: Boards (A Unique Aspect of the CEO’s Job)
5.1          Building Your Board
5.2          Meeting Materials
5.3          Meetings
5.4          Between Meetings
5.5          Making Decisions and Maximizing Effectiveness
5.6          The Social Aspects of Running a Board
5.7          Working with the Board on Compensation
5.8          Evaluating the Board
5.9          Serving on Other Boards
5.10       How Boards Change over Time

6           Part Six: Managing Yourself So You Can Manage Others
6.1          Creating a Personal Operating System
6.2          Working with an Executive Assistant
6.3          Working with a Coach
6.4          Finding Your Voice
6.5          The Importance of Peer Groups
6.6          Your Family
6.7          Taking Stock
6.8          Staying Fresh
6.9          Staying Healthy
6.10       Traveling

Book Shorts:  Fred the Cow?

I enjoyed two interesting, super-quick reads from last week that have a common theme running through them:  being remarkable.

The Fred Factor, by Mark Sanborn, is one of those learn-by-storytelling business novellas.  It’s all about the author’s mailman, Fred, and how Fred has figured out how to make a difference in people’s lives even with a fairly routine job.  The focal points of the book are things like “practice random acts of kindness” and “turn the ordinary into the extraordinary by putting passion into your work.”  It’s a good reminder that it is unbelievably easy, not to mention free, to be kind and thoughtful, and that those things are always always always worth doing.  Kinda makes me wonder what the Brad factor is.  <g>

The Big Moo, a collection of essays written by 33 different business thinkers/writers and edited by Seth Godin, isn’t out yet, but you can pre-order it via that link on Amazon.  It follows the main theme of another of Seth’s books, Purple Cow, about how to make your business remarkable and backs it up with various vignettes from the different writers.  It has some great reminders about how easy and inexpensive it can be to be remarkable in business.  Wisdom like “Criticism?  Internalize it,” and “Get great ideas about your business from new employees,” and “How would you run your business if you relied on donations from your customers in order to survive?” are all insightful and thought provoking.

Each is great and an easy read, and while one is more personal and the other business-oriented, in they are both somewhat remarkable.

(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