(This post was inspired by Startup CXO and was originally published by Techstars on The Line.)

In most startups, one of the founders is the first salesperson — often out of necessity as much as passion. But as startups scale they add sales reps or maybe some form of a Sales Manager once there are more than a couple of reps. But how do you know when to bring on a senior sales leader? Too soon and you have a very expensive employee, too late and your sales reps are creating their own processes and approaches. As a CEO there are several telltale signs that you need to hire a CRO, for example:

• You wake up in the middle of the night concerned about HOW you’re going to make this quarter’s number. You have no clue about what the levers are, or what the pipeline/forecast details are, to get there.
• You are spending too much of your own time managing individual deals and pricing, or teaching individual reps how to get jobs done.
• Your Board asks you if you’re ready to step on the gas and scale your revenue engine and you don’t have a great answer and aren’t sure how to get to one.

But don’t wait until you’re waking up in the middle of the night to hire a CRO. Instead, use this simple process to build some consistency in your sales team and set yourself up to scale rapidly when the time comes.

Building a Sales Team: From “Whiteboard” to “PDF”

There is a framework we learned from one of our original investors at Return Path, Greg Sands. Greg always talked about the evolution of an enterprise selling process as going from “selling on whiteboard, to Powerpoint, to PDF.” A “Whiteboard” approach to sales is one that is exploratory and conceptual. A “Powerpoint” approach is a sale that requires creativity and tailored pitches, while a “PDF” sale is a standard sale that can be taught quickly to an inexperienced sales rep and used with a high degree of predictability to all customers.

Many startups think that they need to be at the PDF stage quickly but as a startup your goal should not be to deliver a polished, buttoned down and refined final PDF to customers. Your goal should be to start with a mindset of discovery.

Whiteboard Sales Approach

Your initial sales team (maybe the CEO and/or Head of Product) should go to a prospect’s office and literally use a whiteboard, drawing things out (drawing charts, and frameworks, and circles, and arrows, and exclamation points), while you try to understand your potential customer’s problem. You’re creating this with the client because you don’t have a deck yet, much less a PDF. It can be very interactive and engaging selling on a whiteboard and using that very intimate moment to try to develop the right story for your product.

Powerpoint Sales Approach

As you evolve and grow, chances are you’ll have a sales deck and a pitch because you won’t be discovering what the customer needs. You’ll have very refined (and tested) ideas about their needs and maybe you’ll even have customer segments. But a caution here is that what could (and often does) happen is that your deck, your pitch, get modified along the way — for every single pitch. So, if you have four salespeople, each of them has a different version on their laptop, and there’s probably no central organizing body yet that has thought about what the tone and tenor of the brand should be.

This is the “Selling with PowerPoint” stage and it’s here that good, clever, senior, business development-oriented salespeople are most successful because they will create custom pitches for each client based on their learned history of what has and has not worked in other places. You are still miles away from being a sales machine and what you need is a level of sophistication and market understanding that enables you to get to a PDF presentation.

PDF Sales Approach

A PDF is something that’s complete, that can’t be modified or altered, and it ensures that everyone’s speaking the same language. At this point you have the kind of consistency and message and positioning that enable you to be repeatable and scalable. You can hire a new, junior sales rep, train them for a few weeks, hand them a prospect list and a pdf, and have a really good sense of that person’s likely productivity.

Of course, selling by whiteboard — and even PowerPoint — is sufficient to a point in time but if you’re thinking about unleashing your product on a massive scale, then you have to get to the point where you have a very smooth presentation and message that you know resonates with the audience.

You might be thinking that you can get your sales team from whiteboard to PDF quickly, that it’s a matter of understanding the process and then executing it. But the reality is that there is no quick way to get from whiteboard to PDF and it’s not a linear process. You can’t put into your business plan that you’ll spend the first six months selling with whiteboard, the next six months selling with PowerPoint, and the next six months selling with PDF. It’s much more nuanced, there’s a lot of trial and error, a lot of experimentation, and a lot of thinking and rethinking based on customer ideas and feedback. At Return Path, for example, it probably took us somewhere between five to ten years before we got from whiteboard to PDF and it was only after refining our approach and materials that we were able to build a sales machine.  

Obviously, a startup can’t wait the five to ten years to hire a CRO, but even at the “Whiteboard” stage an inquisitive person, excited about your product and customers, could help build and grow a dynamic sales team… and certainly by the “Powerpoint” stage, a strong senior sales leader can make a world of difference — and drive you to the “PDF” stage.

Email Articles This Week

I know, not a real inspired headline.  There are two interesting articles floating around about email marketing this week.  I have a few thoughts on both.

First, David Daniels from Jupiter writes in ClickZ about Assigning a Value to Email Addresses.  David’s numbers show that 71% of marketers don’t put a value on their email addresses.  I think that may be an understatement, but it’s a telling figure nonetheless.  David’s article is right on and gives marketers some good direction on how to think about valuing email addresses.  The one thing he doesn’t address explicitly, though, is how to think about the value of an email address in the context of a multi-channel customer relationship.  Customer Lifetime Value is all good and well, but the more sophisticated marketers take the next step and try to understand by customer (or segment) how valuable email is relative to other channels.

Second, David Baker writes in Mediapost’s Email Insider about Finding New Customers Via Email.  The column is a nice discussion of how important email is to retaining customers.  We at Return Path completely agree.  However, the question Baker posed at the beginning is not well addressed — “Should I use email to find new customers?”

My company works with hundreds of smart marketers every week who say, “Yes!  Because it’s effective, cost efficient and is the only way to combine the relevancy of search with the power of online advertising.”

I applaud Baker’s note of caution to marketers planning to acquire customers via email.  It’s always a good idea to plan the campaign with the same diligence you plan any marketing outreach — making sure the targeting, message, design and offer are all optimized for the prospect interest and the medium.

However, I take great issue with his conclusion that email acquisition marketing “does more harm than good.”  Our clients disprove this claim every day.  Email prospecting done well includes a synergy of organic, viral and paid techniques.  Consumers and business professionals still want to receive relevant and informative offers via email.  More than 50,000 of them sign up every DAY for email offers from Return Path alone.

Poeple who have failed list rental tests (and there are lots of them) need to ask some hard questions of their campaign strategy, their creative, their list rental partner, and their agency.  Did you try to send the same message and design to a list of prospects as you do to your house file?  No wonder no one got the message, they don’t even know you.  Was your list double opt-in?   Did you segment the list by interest category or demographics?  Perhaps your message was mis-targeted.  Did your landing page make it easy to take advantage of the offer?  Did you test on a small portion of the list before blasting the entire file?  Did you optimize your subject line to ensure higher open rates?  Did you try to do too much?  The golden rule of email list rental is “one email, one message.”

The success of many marketers using list rental today can not be ignored.  Done well, email acquisition is extremely powerful.  And, the addition of new lead generation, co-registration and offer aggregation opportunities create even more custom and targeted opportunities to connect with prospects.

It’s too easy to dismiss something that didn’t work two years ago by blaming the medium.  Instead, recognize that old experience for what it was.  A well-intentioned effort to test out a new medium, that didn’t work because many tried to apply practices from other media to it.  Times have changed, and email acquisition has proven its value.

Stick with Daniels’ article, figure out how valuable an email address can be for you, then go out and collect as many of them as you can from customers and prospects who will be all-too-willing to give them to you in exchange for content, offers, and other points of value.

• Not all successful CEOs are extroverts: Financial News – Yahoo! Finance
  Brad tipped me off to this article — it’s a good one and draws on a lot of the work and thinking done by Jim Collins in both Good to Great and Built to Last (links to both books on my blog in the books sidebar).
  (tags: Books Entrepreneur Management)

Everyone’s a Marketer, Part I

While there’s a specific marketing department at most companies, I think in today’s inter-connected, service-oriented business, everyone in the company is a marketer. Ok, it’s probably more true in some industries than others, but consider these pockets of marketing activity from non-sales/marketing personnel:

– Our front line customer service manager, Anthony, is on the phone with hundreds of customers each week answering questions about their email subscriptions or helping them unsubscribe. His mission? Make sure they understand our services and try to get as many of them as possible to stay on with us.

– Our client data coordinators Jeremy and Tom talk and email with clients regularly as we send data back and forth for processing. They have an ever-present opportunity to ask clients for more data, to talk to them about their email programs, to give them advice or help on their business.

– Any receptionist greets people every day on the phone and in person. How many of those people’s first impressions of your company come from this individual? How many of those who call or stop by are customers or potential customers?

– Our database administrator Kevin and our head of product management and quality assurance Dan talk to customers about their needs for reporting, or for custom functionality, not just trying to get the answer but trying to understand the business drivers behind the needs and think about the implications of those needs for other customers.

– Any hiring manager or recruiter is doing screening interviews with candidates for a new position. One of those candidates will end up as the “chosen one” — meaning our recruiter has to be selling that person (and therefore all candidates since the winner is unknown at the outset) on how great our company is from first contact.

– Our accounting team Liz and Paul call clients when they have overdue bills. Getting this right is a true art form — it’s tough to simultaneously be The Enforcer and also express appreciation for the customer’s business.

All of these things sound distinctly like marketing to me. So, with all of this non-marketing marketing going on, what should a smart company do? Weave the work of the marketing department into the daily lives of all employees: make sure everyone knows core messaging and value propositions, teach everyone to think like a marketer, provide easy mechanisms for people to report market feedback and needs into the marketing department.

We don’t do nearly enough of this at Return Path, but we have it as a goal to improve on these things.

Next up in this series: marketing yourself.

Counter Cliche:  As Simple As the Wheel

Fred’s VC cliche of the week this week is about the analog analog.  It builds on one of Brad’s great concepts which he blogged about here.  The concept is that figuring out how a digital idea mirrors an offline idea is a better way of handicapping future success of a venture than understanding pure technology analogs. 

I tend to agree with Fred, that it’s one useful lens with which to evaluate a new idea, but not the only one.  So my counter cliche for the week is to look for something As Simple As the Wheel. 

At Return Path, by the way, nearly every business we’re in has a clear analog analog (Email Change of Address = Postal Change of Address, Email List Rental = Postal List Rental, Email Market Rearch = Telephone Market Research, and on and on) and has been the result of real brainstorming processes and complex, nuanced thinking.

But innovation doesn’t have to be all that complex.  One of my favorite examples of this is luggage.  Somehow, for decades, we all travelled with suitcases or garment bags or duffel bags creating pinched nerves as they hung from our shoulders or bad backs as we gripped them and sprinted through airports.

Then someone decided to put litle wheels on luggage and change the luggage industry and the way we travel for the better.  WHEELS, for goodness sake.  Not ASP, not B2B, not CRM, not ERP, not the human genome project, not cold fusion.

What’s the wheel that your industry or product needs?  Don’t search for the analog analog if there’s something more simple staring you in the face that can explode your market.

Sender Score:  Credit Scores for Emailers

Yesterday, I wrote about email authentication, and why, although it’s great, it won’t stop spam without the emergence and scaling of accreditation and reputation systems.

Today, Return Path has announced the beta launch of Sender Score, our new reputation management system.  Sender Score is a groundbreaking service that we’ve been working on for a long time here.  The best way to think about it (or the analog analog, as Brad might say) is as a FICO or credit score for email.

We’ve gone out and compiled TONS of data about emailers, much as the credit bureaus do when they gather financial profile and transaction data about individuals and businesses.  But our data, when aggregated and modeled, represents an emailer’s reputation — are they a “good risk” to let into your email network, or are they a “bad risk” to be treated separately?

What kind of data?  It’s the same data that ISPs and sys admins use to block and filter most emailers…variables such as complaint data, e-mail send volume, unknown user volume, security practices, identity stability, and unsubscribe functionality.  The system tracks 60 different data points and draws data from a diverse sample of more than 40 million email boxes.  The data comes from lots of different places, some from our own systems, and some from partner ISPs and other tech/filtering/data companies we’ve partnered with such as Cloudmark and Lashback.

This is powerful stuff.  The main thing we do with the data is provide it back to email marketers and publishers in a format that’s easy to understand and act on.  It’s like the free credit report many banks offer their customers so their customers can see themselves as potential creditors see them, then work to shore up the weak spots in their profile so they’re more likely to get the next loan/mortgage/approval.

Sender Score rounds out our Delivery Assurance offerings by adding reputation management to accreditation, monitoring, and professional services offerings.  With authentication gaining steam out there as a backdrop to all of this…we’re a lot closer to solving spam and false positives than we’ve ever been.

Americans have long operated under an unwritten deal with media companies (for our purposes here, let’s call this the Old Media Deal). The Old Media Deal is simple: we hate advertising, but we are willing to put up with an amazing amount of it in exchange for free or cheap content, and occasionally one of those ads slips through to the recesses of our brain and influences us in some way that old school marketers who trade in non-addressable media can only dream of. Think about it:

– 30 minutes of Friends has 8 minutes of commercials (10 in syndication!)
– The New York Times devotes almost 75% of its total column inches to ads
– We get 6 songs in a row on the radio, then 5 minutes of commercials
– The copy of Vogue‘s fall fashion issue on my mom’s coffee table is about 90% full page ads

The bottom line is, advertising doesn’t bug us if it’s not too intrusive and if there’s something in it for us as consumers.

Since I started working in “New Media” in 1994, I’ve thought we had a significantly different New Media Deal in the works. The New Media deal is that we as American consumers are willing to share a certain amount of personal information in exchange for even better content, more personalized services, or even more targeted marketing — again, as long as those things aren’t too intrusive and provide adequate value. Think about how the New Media Deal works:

– We tell Yahoo that we like the Yankees and that we own MSFT stock in order to get a personalized home page
– We tell Drugstore.com what personal health products we buy so we can buy our Q-tips and Benadryl more quickly
– We tell The New York Times on the Web our annual income in order to get the entire newspaper online for free
– We let PayTrust know how much money we spend each month so that we can pay our bills more efficiently
– We let Google scan our emails to put ads in in them based on the content to get a free email account
– We give their email address out to receive marketing offers (even in this day and age of spam) by the millions every day

Anyway, after a few years of talking somewhat circuitously about this New Media Deal, my colleague Tami Forman showed me some research the other day that backs up my theory, so I thought it was time to share. In a study conducted by ChoiceStream in May 2004, 81% of Internet users expressed a desire for personalized content; 64% said they’d provide insight into their preferences in exchange for personalized product and content recommendations; 56 would provide demographic data for the same; and 40% said they’d even agree to more comprehensive clickstream and transaction monitoring for the same. All of these responses were stronger among younger users but healthy among all users. Sounds like a New Media Deal to me.

Don’t get me wrong — I still think there’s a time and a place for anonymity. It’s one of the great things about RSS for certain applications. And privacy advocates are always right to be vigilant about potential and actual abuses of data collection. But I think it’s becoming increasingly clear that we have a New Media Deal, which is that people are willing to sacrifice their anonymity in a heartbeat if the value exchange is there.

P.S. Quite frankly, I wish I could give spammers a little more personalized information sometime. They’re going to email me anyway — they may as well at least tell me to enlarge a part of my body that I actually have.

OnlyOnce is Ok

Fred and Brad from Union Square Ventures have a great post today about the kinds of entrepreneurs they like to back and why.  I particularly like it because almost half their portfolio is made up of companies led by first-time CEOs, which as you probably know, is one of the founding themes around this blog.

Why Do Companies Sell?

Fred has a good post today about Facebook and why they shouldn’t sell the company now, in which he makes the assertion that companies sell “because of fear, boredom, and personal financial issues.”  He might not have meant this in such a black and white way, and while those might all be valid reasons why companies decide to sell, let me add a few others:

• Market timing:  As they say, buy low – sell high.  Sometimes, it’s just the right time to sell a business from the market’s perspective.  Valuations have peaks and troughs, and sometimes the troughs can last for years.  Whether you do an NPV/DCF model that says it’s the right time to sell, or you just rely on gut (“we aren’t going to see this price again for a long time…”), market timing is a critical factor
• Dilution:  Sometimes, market conditions dictate that it isn’t the best time to sell, BUT company conditions dictate that continuing to be competitive, grow the top line, and generate long-term profits requires a significant amount of incremental capital or dilution that materially changes the expected value of the ultimate exit for existing shareholders (both investors and management)
• Fund life:  Fortunately, we haven’t been up against this at Return Path, but sometimes the clock runs out on venture investors’ funds, and they are forced into a position of either needing to get liquidity for their LPs or distribute their portfolio company holdings.  While neither is great for the portfolio, a sale may be preferable to a messy distribution

Fred’s reasons are all very founder-driven.  And sometimes founders get to make the call on an exit.  But factoring in a 360 view of the company’s stakeholders and external environments can often produce a different result in the conversation around when to exit.

Brad wrote a fun post a couple years ago about rituals, including one about The Annual Dinner that he and Amy, Fred and Joanne Wilson, and Mariquita and I have been having not quite annually for almost 15 years now.  His most poignant comment (other than that apparently he and I are both getting larger and greyer in sync with each other) is about the power of marking the passage of time together with the same group of people.  We have a similar tradition at Return Path that’s worth noting in the context of my reboot program since it happened a few weeks ago and was part of the reboot cycle.

On the first anniversary of Return Path’s founding, I took my co-founder Jack Sinclair and our first two colleagues, Matt Spielman and Alexis Katzowitz, our to lunch where we shared lessons learned from the past year at the company and predictions for the company in the coming year with each other.  Jack, George Bilbrey, and I continued doing an end-of-year meal tradition with those two conversation topics for over a decade.  The last three years, since Jack left to join Stack Overflow, George and I have continued the tradition on our own.  Although some of our conversation every year isn’t really for public consumption, I’ve always regretted not blogging some highlights of it.  The tradition is a very powerful one of reflection and retrospective, which is deeply ingrained in Return Path’s culture, as a means of continuous improvement through renewal and refreshing.

Last month, we came up with a few good lessons learned that are featuring in my reboot.  Here they are:

• Growth covers up a lot of weaknesses.  While we still have a healthy growth rate as a company, it’s lower than is used to be – as is the case for all companies as they grow and face the law of large numbers.  What’s interesting, though, is how many weaknesses growth can cover up that start getting exposed as growth slows.  Think of it as an analogy to Technical Debt, call it Organizational Debt.  It’s the accumulation of small decisions over time to take an expedient path on a particular item.  It’s the “oh, we’ll throw a body at the problem now and automate the solution later” type thing that never gets automated, then gets compounded when the hired body needs to be replicated, then managed, then turned into a department.  You get the idea.
• Executive playbooks must be applied flexibly.  As is true of many growing companies, we’ve hired a number of outside senior executives over the last few years.  Some have worked out and others haven’t.  One thing we’ve learned, though, is that there’s a bit of a myth sometimes around the “I have the playbook” claim, the same way there’s a myth around hiring sales people who claim “I have a Rolodex” (or whatever the current version of that is).  Every company is unique, even in the same space.  Every situation is unique.  What makes an executive great is the ability to take learnings and experiences from prior roles and companies, both good and bad, and apply them thoughtfully to new situations, not the ability to run the same play over and over again in exactly the same way.  Sure, there are core business processes or systems that can be applied consistently, but most of those don’t require senior executive expertise.
• Know the job your customer is hiring you to do and what the alternatives are.  This is contemporary product management language, but it really rings true.  No matter who you are, no matter what job you do, you have a customer.  That customer is paying you something for a reason.  That money could go somewhere else.  Keeping that reason top of mind (and understanding when and why and how it shifts) is critical to developing the right solutions.

George, thanks for a decade and a half of reflections together (among other things!).

I heard two great lines recently applied to CEOs that are thought provoking when you look at them together:

You have to care about everything more than anything

and

You can do anything you want but not everything you want

Being a CEO means you are accountable for everything that happens in your organization. That’s why you have to care about everything. People. Product. Customers. Cash flow. Hiring. Firing. Board. Fundraising. Marketing. Sales. Etc. You can never afford not to care about something in your business, and even if there’s a particular item you’re more focused on at a given point in time, you can never get to a place where you care about any one particular thing more than the overall health of the business.

But caring is different than doing. As a CEO, even if you’re hyper productive, you can’t do everything you want to do – and you shouldn’t. Others in your organization have to take ownership of things. And you can’t burn yourself out or spread yourself too thin. But you do have the prerogative of doing anything you want in and around your company as long as you do it the right way.

This second line is particularly interesting when applied to a CEO’s activities outside of work. As with anyone, it’s critical for CEOs and founders to have outside hobbies and interests, time for friends and family, down time, and even non-work work time like sitting on outside boards. Staying fresh and “sharpening the saw” is good for everyone. A CEO should be able to do anything she wants outside of work — from sitting on outside boards to being in a band. But a CEO can’t do everything she wants outside of work while still devoting enough time and attention to work.

Taken together, the two lines are interesting. As a CEO, you have to care about everything, but you can’t do everything. That pretty much sums up the job!