As I finished up my work on the Second Edition of Startup CEO:  A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons.  The book is called Startup CXO:  A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company?  If you’re leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about?  What does ‘great’ look like?  What challenges lurk around the corner as you scale your function that you might not be focused on today?  If you’re a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people?  If you’re an aspiring executive, from entry-level to manager to director, what do you need to think about as you grow your career and develop your skills?

Startup CXO is a “book of books,” with one section for each major function inside a company.  Each section is be composed of 15-20 discrete short chapters outlining the key “playbooks” for each functional role in the company – Chief People Officer, Chief Financial Officer, Chief Marketing Officer, Chief Revenue Officer, etc., hence the title Startup CXO – which is a generally accepted label in the startup ecosystem for “Chief ____ Officer.”

Here are the front and back covers of the book, with some great endorsements we’re so proud of on the back.

This is an important topic to write about at this particular time because America’s “startup revolution” continues to gather steam.  There are only increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures.  While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books about the topic of Sales, the topic of Product Development), there are very few books that are practical how-to guides for any individual function, and NONE that wrap all these functions into a compendium that can be used by a whole startup executive team.  Very simply, each section of this book serves as a how-to guide for a given executive, and taken together, the book will be a good how-to guide for startup executive teams in general.

Startup CXO has my name on it as principal author, and I’m writing parts of it, but I can’t even pretend to write it on my own, so the book has a large number of contributors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines — most of my Bolster co-founders are writing sections, and the others are being written by former Return Path executive colleagues — Jack Sinclair, Cathy Hawley, Ken Takahashi, Anita Absey, George Bilbrey, Dennis Dayman, Nick Badgett, Shawn Nussbaum, and Holly Enneking.

Startup CXO is also pretty closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent, and as such, the final section of the book has a series of chapters written by Bolster members who are career Fractional Executives about their experience as a Fractional CXO.

The book is available for pre-order now at Amazon and Barnes & Noble.

Oh, and stay tuned for a third book in the series (kind of) due out late this year. More on that over the summer as the project takes shape!

At my last company, we used to occasionally attend a giant meeting at one of the large ISPs — Microsoft, Yahoo, and the like — and it always annoyed me to be presenting to or engaging in a discussion with a room full of a dozen people and having all of them there with their laptops open, clearly distracted and doing other work.

I’m increasingly finding annoyance with the Zoom equivalent, which is being in a meeting or attending a presentation, but turning off your mic and camera.

It’s impossible to know as the person leading the meeting or speaking if you’re actually there. And if you’re there, if you’re paying attention. And how many times in a meeting can we hear “Joe, you’re on mute”?

We do occasionally invite people to lurk at meetings intentionally. Maybe a meeting is really long, it contains a range of topics, some are going to be relevant for a given person and some aren’t. We explicitly note that it’s ok to “Bolster down” (as we call it) for a given meeting, and just turn on your camera and mic if you want to be in the conversation, otherwise, the assumption is you’re half listening and multitasking, and you can be asked specifically to “Bolster up” at any time.

But otherwise, if a meeting is worth going to, or if a small group presentation is worth going to, leave your camera on, and unless you have a dog barking, a baby crying, or a lawnmower humming in the background, leave your mic on. In other words…

Be present.

Less is More

I have a challenge for the email marketing community in 2009. Let’s make this the Year of “Less is More.”

Marketers are turning to email more and more in this down economy. There’s no question about that. My great fear is that just means they’re sending more and more and more emails out without being smart about their programs. That will have positive short term effects and drive revenues, but long term it will have a negative long term impact on inboxes everywhere. And these same marketers will find their short term positive results turning into poor deliverability faster than you can say “complaint rate spike.”

I heard a wonderful case study this week from Chip House at ExactTarget at the EEC Conference. One of his clients, a non-profit, took the bold and yet painful step of permissioning an opt-out list. Yikes. That word sends shivers down the spine of marketers everywhere. What are you saying? You want me to reduce the size of my prime asset? The results of a campaign done before and after the permission pass are very telling and should be a lesson to all of us. The list shrank from 34,000 to 4,500. Bounce rate decreased from 9% to under 1%. Spam complaints went from 27 to 0 (ZERO). Open rate spiked from 25% to 53%. Click-through from 7% to 22%. And clicks? 509 before the permissioning, 510 after. This client generated the same results, with better metrics along the way, by sending out 87% LESS EMAIL. Why? Because they only sent it to people who cared to receive it.

This is a great time for email. But marketers will kill the channel by just dumping more and more and more volume into it. Let’s all make Less Is More our mantra for the year together. Is everyone in? Repeat after me…Less Is More! Less Is More!

Book Short:  Vive La Difference

Brain Sex, by Anne Moir and David Jessell, was a fascinating read that I finished recently.  I will caveat this post up front that the book was published in 1989, so one thing I’m not sure of is whether there’s been more recent research that contradicts any of the book’s conclusions.  I will also caveat that this is a complex topic with many different schools of thought based on varying research, and this book short should serve as a starting point for a dialog, not an end point.

That said, the book was a very interesting read about how our brains develop (a lot happens in utero), and about how men’s and women’s brains are hard wired differently as a result.  Here are a few excerpts from the book that pretty much sum it up (more on the applied side than the theoretical):

• Men tend to be preoccupied with things, theories, and power…women tend to be more concerned with people, morality, and relationships
• Women continue to perceive the world in interpersonal terms and personalize the objective world in a way men do not.  Notwithstanding occupational achievements, they tend to esteem themselves only insofar as they are esteemed by those they love and respect.  By contrast, the bias of the adult male brain expresses itself in high motivation, competition, single-mindedness, risk-taking, aggression, preoccupation with dominance, hierarchy, and the politics of power, the constant measurement and competition of success itself, the paramountcy of winning
• Women will be more sensitive than men to sound, smell, taste, and touch.  Women pick up nuances of voice and music more readily, and girls acquire the skills of language, fluency, and memory earlier than boys.  Females are more sensitive to the social and personal context, are more adept at tuning to peripheral information contained in expression and gesture, and process sensory and verbal information faster.  They are less rule-bound than men
• Men are better at the kills that require spatial ability.  They are more aggressive, competitive, and self-assertive.  They need the hierarchy and the rules, for without them they would be unable to tell if they were top or not – and that is of vital importance to most men

As I said up front, this book, and by extension this post, runs the risk of overgeneralizing a complex question.  There are clearly many women who are more competitive than men and outpace them at jobs requiring spatial skills, and men who are language rock stars and quite perceptive.

But what I found most interesting as a conclusion from the book is the notion that there are elements of our brains are hard wired differently, usually along gender lines as a result of hormones developed and present when we are in utero.  The authors’ conclusion — and one that I share as it’s applied to life in general and the workplace in particular — is that people should “celebrate the difference” and learn how to harness its power rather than ignore or fight it.

Thanks to David Sieh, our VP Engineering, for giving me this book.

Ten Characteristics of Great Investors

Fred had a great post today called Ten Characteristics of Great Companies.  This link includes the comments, which numbered over 70 when I last looked.  Great discussion overall, especially for Fred’s having come up with the list on a 15-minute subway ride.  Fred used to write a series of posts about VC Chiches, and I would periodically write a Counter-Chiche post from the entrepreneur’s perspective.  This post inspired me to do the same.

So I’ve taken 15 minutes here, pretended I’m on the subway, and here is my list of Ten Characteristics of Great Investors, in no particular order:

1. Great investors know how to give strategic advice without being in the operating weeds of a company
2. Great investors get to know whole management teams, not just CEOs — in fact, great investors become part of the extended management team of their portfolio companies
3. Great investors invite you to do diligence on them by giving you a list of every CEO they’ve ever worked with and asking you to pick the ones you want to talk to
4. Great investors ask great questions
5. Great investors don’t publicly take credit for the success of their investments, even if they were major drivers of that success
6. Great investors show up for meetings on time and don’t spend the meeting using their smartphone
7. Great investors treat their portfolio companies’ money as if it were their own money when spending it on things like lawyers or travel
8. Great investors look for connections to make between their portfolio companies or relevant people but have a strong relevance filter and don’t send junk
9. Great investors never have a ready-made list of the ways they add value to companies — and they specifically never talk about the help they give in recruiting executives or making sales/bus dev introductions
10. Great investors recognize when they have a conflict around a portfolio company and are clear to represent their separate points of view separately

I’m not sure I’ll be invited to present this anywhere, but there it is for discussion.

Managing by Checklist

The Checklist Manifesto:  How to Get Things Right, started as an article in The New Yorker a few years ago by Atul Gawande and then turned into a book as well (book, Kindle).  I haven’t read the book; the story in the article is about life-and-death issues and how Intensive Care Units in hospitals work most successfully when they “manage by checklist” — they keep thousands of small steps performed by different people in order.

The story is very telling for business as well and reminiscent of David Allen’s productivity books, Getting Things Done: The Art of Stress-Free Productivity and Ready for Anything: 52 Productivity Principles for Work and Life. The reality as far as I’m concerned is that no matter who you are, no matter what role you play in an organization, my guess is that there are some routine or recurring tasks you perform where having a tight checklist is a no-brainer.  Between eliminating missed steps and increasing productivity by not having to reinvent the wheel…we may not be saving lives in dramatic fashion in most businesses, but we all have jobs to do and want to do them as well as possible.

Thanks to my colleague Tami Forman for pointing me to this.  At a minimum, the article is a great read.  And oddly, I had this post drafted for quite a while – I decided to post it today when I saw Jeff Ogden’s post about the same topic in reference to yesterday’s emergency landing at JFK.

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.