4 Things Most Founders Get Wrong About Marketing with Dave Kellogg

So at SaaStr Annual, Dave Kellogg did a great deep dive on “5 Things Every B2B CEO Needs to Know about Marketing”.  In the Age of AI it’s even more true today, so I wanted to update our SaaStr take-aways from the deep dive.

And see everyone at 2025 SaaStr Annual, May 13-15 in SF Bay for 300+ more sessions, workshops, and braindates like this!

About Dave Kellogg

Dave Kellogg brings a rare combination of marketing and executive leadership experience to his analysis of SaaS businesses. With 10+ years as a CMO at companies ranging from $1M to $1B in revenue, another 10+ years as CEO of companies in the $0-$100M range, and extensive experience as an independent director on startup boards, Dave offers a 360-degree perspective on marketing’s role in SaaS success.

The 4 Things Most Founders Get Wrong About Marketing:

1. “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. You founded a product company, but you’re running a distribution business.
2. “Marketing is fluffy and unmeasurable” – Unlike sales, which has clear metrics like quota attainment, founders often believe marketing can’t be measured. In reality, effective marketing is deeply analytical and data-driven, with clear KPIs at every funnel stage.
3. “More leads = better marketing” – Many founders obsess over lead volume while ignoring lead quality. A smaller number of high-quality leads that convert at higher rates is vastly superior to a flood of poor-fit prospects.
4. “We just need one great CMO who can do it all” – Founders often search for a marketing unicorn who excels at brand, demand gen, product marketing, and digital programs. These “five-five” CMOs barely exist. Better to hire for your specific needs and stage.

Top CMO Learnings:

1. The CMO should be the quarterback of your pipeline – They’re the only executive with visibility across all four pipeline sources (Marketing, SDR outbound, Alliances, and Sales outbound).
2. The marketing session is often “career-ending” for CMOs – The quarterly marketing review tends to run overtime, spark intense debates, and is the most dreaded session for many CEOs who aren’t marketing natives.
3. Marketing people come in “flavors” – Most CMOs specialize in 1-2 areas across four pillars (Product Marketing, Demand Gen, Digital Programs, and Brand). The “five-five” CMO who excels at everything is a unicorn.
4. For high-consideration purchases, “long copy sells” – Despite our short attention span world, buyers of enterprise software will read your 12-page white paper and attend hour-long demos if they provide valuable information.

The B2B Reality Check: You’re Running a Distribution Company

If you’re a typical founder, your journey began with identifying an unserved need in the market. You assembled a talented team, built an amazing product, and established a growing SaaS business.

Then one day, while reviewing your P&L, you had a moment of clarity (or perhaps shock): you’re spending twice as much on sales and marketing as you are on R&D. This wasn’t what you signed up for when founding a “product company,” was it?

But here’s the reality check: this is completely normal in SaaS. The median enterprise SaaS company spends 2x on sales and marketing compared to R&D, and 9 out of 10 SaaS companies spend more on sales and marketing than R&D. In fact, 50% of SaaS companies spend more than double.

Let’s look at some real-world examples:

• Salesforce spends 3x as much on sales and marketing as R&D
• Smartsheet and HubSpot spend 2-2.4x as much
• Zoom spends 4x as much
• Monday.com, despite being product-led, spends a staggering 5x as much

The truth? You might have founded a product company, but you’re running a distribution company.

Why Marketing Sessions Are a CEO’s Nightmare

For many CEOs, especially technical founders, the marketing session is the most dreaded part of the Quarterly Business Review (QBR). It typically:

• Runs overtime, often dramatically
• Leaves attendees confused and disoriented
• Sparks intense debates
• Can be career-ending for the head of marketing

Why is this the case? For product-oriented founders, marketing often feels like unfamiliar territory. The buzzwords, the acronyms, the endless numbers around conversion rates and funnels, the ill-defined terminology — it all contributes to the intimidation factor. Mix in the classic conflict between sales and marketing teams, and you’ve got a recipe for disaster.

Many CEOs are afraid to admit they don’t understand marketing concepts, so they simply move on to the next session and continue to leave marketing decisions to others. But there’s a better way.

The 5 Things Every CEO Must Know About Marketing

With experience as both a CMO (10 years at companies ranging from $1M to $1B in revenue) and a CEO (10+ years leading companies from $0-$100M), I’ve identified five critical concepts that every CEO should understand about marketing.

This isn’t a generic Marketing 101 course. It’s a guide based on real-world experience working with startups, focusing on common mistakes and challenges. It’s designed to help CEOs and C-level executives understand marketing and work effectively with their marketing teams.

Two underlying themes run throughout this guide:

1. Use market research – Don’t rely solely on internal data, which only captures people who’ve interacted with your systems
2. Keep things simple – Avoid getting sucked into complexity

1. Reverse Engineer Marketing from Buyer Empathy

Great marketing starts with understanding the buyer’s state of mind. There are two fundamental questions to consider:

“Why buy mine?” – This is a differentiation message

• Example: Southwest’s “Bags fly free” campaign
• Relevant when the buyer has already decided to purchase a product but needs to choose between vendors
• Appropriate for established categories

“Why buy one?” – This is a value message

• Example: Campbell Soup’s “Soup is good food” campaign
• Relevant for early-stage startups where buyers aren’t sure if they should buy the product at all
• Necessary when you’re creating a new category

How do you determine which question is relevant to your situation? Listen to sales calls or conduct market research to understand if your category has formed yet.

Also crucial: understanding the consideration level of your purchase. This isn’t just about price—it’s about the importance of the purchase and how much time/energy buyers will invest in making the right decision.

For high-consideration purchases (like enterprise software):

• Buyers will read in-depth content
• David Ogilvy’s “long copy sells” still applies
• Produce a mix of long and short content, but don’t shy away from comprehensive white papers (8-12 pages)

To truly understand your buyer:

• Imagine yourself as the buyer
• Consider where they’d go for information
• Understand their decision-making process
• Ask customers about their buying process

2. Marketing Is All About Funnels

There are several critical funnels to understand:

The Awareness-Consideration-Trial-Purchase Funnel

• Awareness: Have they heard of your product?
• Consideration: Have they thought about buying it?
• Trial: Have they tried it?
• Purchase: Have they bought it?

This funnel can only be analyzed through market research—it won’t show up in your CRM.

The Marketing and Sales Funnel

• Web traffic → Leads → MQLs → SQLs → Opportunities → Closed Deals
• Track conversion rates between stages
• Protect your pipeline with a two-key system (BDR and salesperson must agree an opportunity is valid)

The Four Pipeline Sources

• Marketing
• SDR outbound
• Alliances (10-30% of pipeline, faster closures, higher success rates)
• Sales outbound (with targeted strategy)

A common mistake: forgetting these four sources exist and failing to develop a comprehensive strategy for each.

Best Practices for Pipeline Management:

• Allocate target opportunity counts to each pipeline source
• Make the CMO the quarterback of the pipeline
• Have the CMO forecast pipeline coverage at least a quarter in advance
• Look for benchmark conversion rates:
  • MQL to S1: 5-10%
  • S1 to S2: 60-80%
  • Stage 2 to close: 10-25%

Use funnel models to build comprehensive plans that incorporate sales capacity, hiring, rep ramp, and attrition—but remember Gartner’s reality check: enterprise software buying involves ~15 contacts across 4 roles in 2 companies over 2 years. It’s messy.

Which brings us to an important principle: “All models are wrong, but some are useful.”

3. Use Models as Guiding Abstractions, Not Tools of Oppression

Models should enlighten, not oppress. The primary mistake founders make is holding people accountable for every aspect of a model.

Instead, focus on two key metrics:

1. Pipeline coverage – Do we have a chance to hit our numbers?
2. Actual sales – Did we hit our targets?

Everything else in the model is just a guide.

To avoid model myopia:

• Conduct quarterly win-loss analysis with a third-party firm
• Perform win-touch analysis to understand the customer journey
  • Have marketing present every single touch made on 3-4 closed deals from the previous quarter

4. Messaging Is a Structured Set of Facts

Messaging provides standard answers to commonly asked questions, based on the 5W+3H principle:

• Who
• What
• Where
• When
• Why
• How
• How much
• How different (critical for tech companies)

Effective messaging should be simple enough to explain on a paper tablecloth. When testing messaging, ask people to draw pictures that convey the message in their head.

Tactical advice:

• Use black and white messaging when on offense
• Use gray messaging when on defense (make the other party explain and justify)
• Follow the rule of threes—the answer to every question should be three points
• Use ternary trees to build complex messages in a simple, memorable way

5. Hire the Right CMO by Understanding Marketing Pillars

With the average CMO tenure being just 1.5-2.5 years, you’ll likely be hiring a new one soon. A common mistake: reaching the final three candidates and realizing they’re all completely different (a demand gen person, a product marketing person, and an SDR leader).

Marketing has four pillars:

1. Product Marketing
   • Positioning
   • Messaging
   • Content
2. Demand Generation
   • Field Marketing
   • Events
   • Customer Marketing
3. Digital Programs
   • SEO/SEM
   • Performance Marketing
   • Web
4. Brand
   • Corporate Identity
   • Creative
   • PR

Most marketing professionals specialize in 1-2 areas and don’t have expertise across all four pillars. Be realistic about what the market has to offer—”five-five” CMOs (experts in everything) are unicorns.

To avoid a flawed search:

• Decide which pillars are most important for your stage
• Map candidates against these pillars
• Choose the profile that best fits your needs

Conclusion

Most SaaS companies spend double on sales and marketing compared to R&D. You’re running a distribution business focused on sales success and marketing.

But marketing shouldn’t be intimidating. Great marketing professionals make it easy and are willing to teach. Remember these five key points:

1. Reverse engineer marketing from buyer empathy
2. Marketing is all about funnels
3. Use models as guiding abstractions
4. Messaging is a structured set of facts
5. Use the pillars framework when hiring marketing talent

These principles will make working with marketing teams easier—and they’ll serve you well when hiring your next CMO.