A few days ago, Steve Pockross released a new episode of his Yes, And Marketing podcast on which he interviews a series of “eclectic and enlivening” marketers where “your weird shower thoughts and disparate liberal arts references take a road trip.” I was last week’s featured guest, and I don’t think the episode fails to deliver on its rather unusual promise.
The importance of rigorous definitions in messaging, and how you can use them to turn gray messages into black-and-white messages.
Walking the benefits stack by repeatedly asking “so what?” and not being afraid to do so.
Never forgetting the kiss, i.e., the ultimate benefit from the point of view of the customer, in your marketing.
Thanks to Steve for having me, to Crispin Read for referring me (his episode is well worth a listen), and to all of you who find the time to listen. While I’ve been doing a lot of podcast interviews of late, like the Grateful Dead, I promise that each show is different. And this one’s a barn burner.
In this fast-paced episode we move through topical discussions of the major SaaS metrics followed by investors and operators alike, and look at the size-segmented benchmarks presented in Ray’s 2020 B2B SaaS Metrics report.
I think the episode is suitable both for the SaaS metrics beginner because we review the basics for most metrics as well as for the grizzled professional because we dive into topical (and sometimes fairly non-obvious) discussions for many of them.
I sometimes get asked about how to structure an enterprise software marketing organization and the relative roles of product marketing vs. competitive analysis. In this post, I’ll share my (somewhat contrarian) thoughts on this topic.
My first job in marketing, which served as my bridge from a technical to a sales-and-marketing career, was as a competitive analyst. Specifically, I was the dedicated Sybase competitive analyst at Ingres in the late 1980s, in a corporate job, but working out of the New York City sales office. Because, at the time, Sybase was a strong new entrant with a beachhead strategy in financial services, this was rough equivalent of working for the Wehrmacht on Omaha Beach on D-Day. I learned not only by watching Sybase’s market invasion, but more importantly by watching how the local reps  and corporate  responded to it.
I’m a huge believer in competitive analysis, which probably started when I first heard this quote watching Patton as an adolescent:
“Rommel, you magnificent bastard, I read your book!” 
While Gekko doesn’t use my favorite quote for these purposes , his reference to the book was very much in vogue at the time, and probably why I first read it. My favorite quote from The Art of War is this one:
“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”
Regular readers know I believe the mission of marketing is to make sales easier. So the question becomes: in enterprise software, how do we structure product marketing and competitive in the best way to do just that?
First, let’s review some common mistakes:
Not specializing competitive, instead declaring that each product marketing manager (PMM) will cover their respective competitors. Too much scope, too little focus.
Understaffing competitive. Even in organizations where competitive exists as its own team, it’s not uncommon to see a ratio of 5-10 PMMs per competitive analyst in terms of staffing. This is too unbalanced.
Chartering competitive as strategic. While I often euphemize the competitive team as “strategic marketing” or “market intelligence,” that’s not supposed to actually change their mission into some think tank. They exist to help sales win deals. Don’t let your competitive team get so lofty that they view deal support as pedestrian.
Putting competitive under product marketing. This both blurs the focus and, more importantly, eliminates a healthy tension . If your messaging doesn’t work in the field, the CMO should want to hear about it early (e.g., in their own staff meeting) and have a chance to fix it before it escalates to the corporate QBR and a potential sales attack on marketing in front of the CEO.
Putting competitive in the field. This happens when marketing abdicates responsibility for producing sales-ready competitive materials and someone else picks up the ball, usually the sales productivity team, but sometimes field marketing . This disconnects corporate product marketing from the realities of the field, which is not healthy.
Now, let’s tell you how I think structuring these departments.
Product marketing exists to build messaging and content  that describe the features and benefits of the product . The job is to articulate. They are experts in products.
Competitive analysis exists to research competitors, devise plays, and build tools to help sales win deals. The job is to win. They are experts in the competitors.
As long as we’re in movie quote mode, here’s one of my favorite quotes from James Mason’s character in The Verdict :
I’d prepared a case and old man White said to me, “How did you do?” And, uh, I said, “Did my best.” And he said, “You’re not paid to do your best. You’re paid to win.”
While he was speaking to about lawyers, he might as well have been speaking to competitive: you’re paid to win.
That’s why I believe competitive needs to be holistic and play-oriented. Simply put, take everything you know about a competitor — e.g., products, leadership, history, tactics — and devise plays that will help you win against them. Then train sales on how to run those plays and supp0rt them in so doing.
If you adopt this mindset you end up with an organization where:
Product marketing and competitive are separate functions, both reporting directly to the CMO
Product marketing is product-oriented, focused on articulation of features and benefits
Competitive is competitor-oriented, focused on using all available information to create plays that win deals and support sales in executing them
Product marketing staffing is driven by the number of products you’re covering
Competitive staffing is driven by the number of competitors you’re covering (and at what depth level or tier).
You end up with a ratio of more like 3:1 than 10:1 when it comes to the relative staffing of product marketing and competitive
You think of these organizations as a matrix:
# # #
 In the case of the reps, their response was to walk away from financial services deals because they knew they were likely to lose. This, of course, had the effect of making it easier for Sybase to enter the market. The smart reps went to Westchester and Long Island and sold in other verticals. The dumb ones battled Sybase on Wall Street, lost deals, missed mortgage payments, broke marriages, and got fired — all for doing what the c0mpany strategically should have wanted them to do: to slow down the invasion. A classic case of micro and macro non-alignment of interests.
 The corporate response was to blame sales management. Rather than seeing the situation as a strategic problem where an enemy was breaking through lines with an integrated strategy (e.g., partners), they chose to see it as an operational or execution problem. Think: we’re hiring bad reps in NYC and losing a lot deals — fire the sales manager and get some new talent in there.
 Good Strategy, Bad Strategy tells the presumably more common inverse tale, where during the Gulf War in 1991 General Schwarzkopf was widely credited with a left-hook strategy described as “surprise,” “secret,” and “brilliant,” that was clearly published in the US Army Field Manual 100-5 saying the following, complete with an illustration of a left hook.
Envelopment avoids the enemy’s front, where its forces are most protected and his fires most easily concentrated. Instead, while fixing the defender’s attention forward by supporting or diversionary attacks, the attacker maneuvers his main effort around or over the enemy’s defenses to strike at his flanks and rear.
 Gekko refers to: “Every battle is won before it’s ever fought.”
 Organization design is all about creating and managing healthy tensions. Such tensions are a key reason why I like marketing reporting to the CEO (and not sales), customer success reporting to the CEO (and not the CRO/sales), and engineering reporting to the CEO (and not product), for a few examples.
 At one point, way back, Oracle had a huge market intelligence organization, but housed within Americas Marketing, a field marketing organization.
 Content being collateral (e.g., web content, white papers, e-books), presentations (internal and external), and demonstrations — all built around communicating the key messages in their messaging blueprint.
 It’s not lost on me that the character was morally bankrupt and was implicitly saying to win at any and all costs. But I nevertheless still love the quote. (And yes, win within normal legal and societal constraints! But win.)
Fortella, which I’ve served as an advisor over the past year or so, makes a revenue intelligence platform. The company recently published an interesting survey report entitled The State of B2B Marketing: What Sets the Best Marketers Apart? Rahul is super passionate about marketing accountability for revenue and the use of AI and advanced analytics in so doing, which is what drew me to want to work with him the first place. He’s also an avid Kellblog reader, to the point where he often reminds me of things I’ve said but forgotten!
In this webinar we’ll drive a discussion primarily related to two Kellblog posts:
That pipeline isn’t a monolith and that we need to look inside the pipeline to see things by opportunity type (e.g., new vs. expansion), customer type (e.g., size segment, industry segment) and by source (e.g., inbound vs. partners). We also need to remember that certain figures we burn into our heads (e.g., sales cycle length) are merely the averages of a distribution and not impenetrable hard walls.
By decomposing pipeline we can identity that some types close faster (and/or at a higher conversion rate) than others, and ergo focus on those types when we are in a pinch.
Lately, I’ve received some consulting inquiries where companies are asking for help with positioning and messaging. While that’s definitely an area of interest and passion, my business model is advice-as-a-service (AaaS) — I work with a smaller set of companies, on a broader set of issues, over a longer period of time. So I’m not really looking for such consulting projects myself.
Thus the purpose of this post is to offer a little quick advice on the subject and then refer readers to three people I’d recommend to help with positioning and messaging in enterprise software.
The three people I’d call for help with positioning would be:
Crispin Read, the single best positioning and messaging person with whom I’ve ever worked. With a scalpel of a marketing mind, he’s not going to tell you what you want to hear, but he will cut through the junk in your thinking and distill your message to its essence. I’m not sure how much consulting he’s doing these days because he’s trying to drive scale with his product marketing community (PMMHive) and Product Marketing Edge. But I’d ping him.
Jeffrey Pease, who runs a NY-based consulting business, Message Mechanics. Like Crispin, he was on the marketing team at Business Objects back in the day, and he is very, very good at messaging. He popped up back in my life via Bluecore who was droning on about this messaging wizard they loved working with — only for me to discover that I’d worked with him in the past. Testimonials on Jeffrey’s website include Bluecore, Coupa, Veeva, and well, Crispin (when he was at Microsoft). So it’s really all just one big, happy positioning family.
April Dunford. This one’s slightly premature — as I’ve not yet finished her book and haven’t worked with her yet. But based on the part of the book I’ve read, her Twitter feed, and her work with related portfolio companies and PE sponsors, I am simply certain that we are kindred positioning spirits and that I’m going to love working with her — as we’re slated to do in upcoming months with one of my portfolio companies.
Good luck, happy positioning, and keep it simple out there.
I’m Dave Kellogg, advisor, director, consultant, angel investor, and blogger focused on enterprise software startups. I am an executive-in-residence (EIR) at Balderton Capital and principal of my own eponymous consulting business.
I bring an uncommon perspective to startup challenges having 10 years’ experience at each of the CEO, CMO, and independent director levels across 10+ companies ranging in size from zero to over $1B in revenues.
From 2012 to 2018, I was CEO of cloud EPM vendor Host Analytics, where we quintupled ARR while halving customer acquisition costs in a competitive market, ultimately selling the company in a private equity transaction.
Previously, I was SVP/GM of the $500M Service Cloud business at Salesforce; CEO of NoSQL database provider MarkLogic, which we grew from zero to $80M over 6 years; and CMO at Business Objects for nearly a decade as we grew from $30M to over $1B in revenues. I started my career in technical and product marketing positions at Ingres and Versant.
I love disruption, startups, and Silicon Valley and have had the pleasure of working in varied capacities with companies including Bluecore, Cyral, FloQast, GainSight, MongoDB, Recorded Future, and Tableau.
I previously sat on the boards of Granular (agtech, acquired by DuPont), Aster Data (big data, acquired by Teradata), and Nuxeo (content services, acquired by Hyland), and Profisee (MDM, exited to Pamlico).
I periodically speak to strategy and entrepreneurship classes at the Haas School of Business (UC Berkeley) and Hautes Études Commerciales de Paris (HEC).