Slides from my SaaStock USA presentation on connecting the c-suite to the ground truth. Discusses both why and how you can do so. How includes [1] deploying CI, [2] doing third-party win/loss, and [3] doing an annual proprietary market study.

1. How To Connect
Your C-Suite To
The Ground Truth
Dave Kellogg
Independent Director, Jiminny*
EIR, Balderton Capital
Author, Kellblog
* See Kellblog FAQ or LinkedIn for other affiliations
All Contents, Copyright © Dave Kellogg 2023, All Rights Reserved.
Revision 1.5
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2. The Ground Truth
What’s actually happening versus what we think, plan, or hope is happening
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3. What’s
Going On?
See: https://en.wikipedia.org/wiki/What%27s_Going_On_(song)
The song's inspiration came from Renaldo "Obie" Benson, a member of the Motown vocal group the Four Tops, after he and the group's tour bus arrived at Berkeley on 5/15/69
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4. Rumelt on
Strategy
“John’s comment was something I had never
heard said explicitly, but it was instantly and
obviously correct. A great deal of strategy
work is trying to figure out what is going on.
Not just deciding what to do, but the more
fundamental problem of comprehending the
situation.”
-- Rumelt, Richard. Good Strategy Bad
Strategy (p. 78)
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5. Why Does Knowing Ground Truth Matter?
• You need to understand execution to validate strategy
• How do you know if you’re in Box 2 or 3?
• Participants bring biases to the conversation
• Management wants to diagnose Box 2
• Board wants to diagnose Box 3
• Founder wants to know if you’re in Box 1 or 3
• Edge of hockey stick or simply “beating” (nautical)?
• Groupthink develops quickly about the reasons
behind problems
• “No one’s ever heard of us.”
• “They don’t see value.”
• “They say we all look the same.”
Box 3
Kinda working
Box 1
Not working
Box 4
Working
Box 2
Kinda working
Execution
Weak
Strong
Strategy
Weak
Strong
See: https://kellblog.com/2022/01/03/why-execution-matters/ 5

6. What is this
seller texting
back to
corporate?
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7. The Problem
• The C-suite can quickly lose touch with the ground truth
• You can’t fix execution problems that you don’t know about
• You can’t assess strategy without understanding execution
• Can start at surprisingly small scale and gets worse as you get bigger
• Why?
• Messaging: see the blueprint, not the house
• Tactics: see the playbook, not the play
• Losses: hear the conventional wisdom, not the horse’s mouth
• Testing: see the certification scores, not the exams
• Demos: see the webinar, not the everyday
• Sales: see closing calls; not the discovery ones
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8. Aside: If You Never Hear Stories Like These, Is
Your Leadership Team Being Transparent?
• “Jesus Phil, this is the third time I’ve asked, just tell me the effing pricing.”
• “Your seller called five minutes before a big meeting and left me a voicemail saying that your company
isn’t interested in our business.”
• “Our seller flew to London, spent 3 days banging out a detailed terms sheet, only to later discover that
he’d painfully negotiated the price, but not the currency ($ vs. £).”
• “The CFO arrived for the big demo but left after 12 minutes because our seller was still presenting
PowerPoints and not showing the software.”
• “All they talked about was us. All you talked about was them.”
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9. Wait, Isn’t CRM Reporting Supposed to Help Us
Figure Out What’s Going On?
And It can only analyze the people we found
and engaged with
But Caveat: requires foundation of discipline
in usage (e.g., definitions, enforcement)
Yes,
Reports and dashboards
Conversion rates, deal velocity, pipeline
progression, stage leakage, win rates, …
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10. Classical CRM
Reporting
See https://en.wikipedia.org/wiki/Navel_gazing
We’re navel gazing, only looking at that
portion of the market who we found
and who chose to engage with us.
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11. Three Recommendations to Connect Your
C-Suite to the Ground Truth
1
Deploy conversation
intelligence software
• Ground truth of messaging
and sales execution
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Do third-party win/loss
reporting
• Ground truth of deals
3
Run annual or inflection-driven
market research
• Ground truth of the market
• Triangulate against CRM reporting
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12. 1. Deploy Conversation Intelligence* Software
• Use software to get insights from customer conversations
• Call recording, transcription, analytics, coaching, forecasting, and more
• Example vendors: Gong, Jiminny**
• I recommend this to literally every startup I work with for the past 5+ years
• Connects the C-suite to sales reality
• Hear the messaging as delivered, hear questions as asked, see tactics and responses,
measure talk/listen ratios, see contact frequency and tone, set alerts (e.g., pricing,
competition), improve forecasting, deliver data-driven coaching
• Ask for clips to support assertions
• Group listening sessions to keep everyone in touch
* Not to be confused with conversational AI or analytics which more describes an interaction or interface style
** I’m on the board of Jiminny and see it as an inexpensive and well-designed alternative to Gong (aka, in British English, a cheap-and-cheerful Gong)
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13. What Happens
When You First
Hear The Sales
Ground Truth?
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14. Layers of Conversation Intelligence Value
Transformation
Process &
Methodology
Analysis & Alerting
Capture Call library, coaching, collaboration
Talk/listen, alerts, tone, topics, frequency, …
Process, frameworks, feedback
Business goals, metrics, and impact
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15. 2. Do Third-Party Win/Loss Reporting
• Hire a third party to interview contacts at
key wins and losses
• Example vendors: Velociti Partners, Growth
Velocity
• Advantages
• Cuts through the “nice” factor
• Eliminates management spin
• Second opinion on the “real” reasons behind
decisions
• Triangulate against CRM reporting on win
rates and loss reasons
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16. 3. Run an Annual* Proprietary Market Study
• Hire a firm to run a proprietary market research study
• Example table of contents
• Market maturity and velocity
• Awareness and lead generation
• Buyer journey
• Value proposition / purchase triggers
• Roles of partners and technology
• Competitive position
• Segmentation / account profiles
• Pricing / packaging
• Revenue potential
• Example vendors: Topline Strategy, King Brown Partners
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* Or an event- or inflection-driven study, as indicated.

17. How to Make the Most of Your Study
• Hire an experienced agency
• Specialists in SaaS working both for vendors and VC/PE community
• Make and maintain a list of questions to answer --- every time you hear:
• An assertion that’s an opinion stated as fact or a question you’d love to know the answer
• Examples
• “Nobody has heard of us compared to our archrival” (awareness/consideration)
• “Buyers are tired of hearing about data culture” (buyer business priorities)
• “People don’t know you can solve data governance with us” (solution awareness)
• “There aren’t enough deals coming to market” (market velocity)
• “If we just had more at-bats we’d make the numbers” (velocity, funnel conversion)
• “People don’t care about the turbo-schmumbleator” (selection criteria)
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See: https://kellblog.com/2021/05/15/navel-gazing-market-research-and-the-hypothesis-file/

18. Conclusion
• Who’d have thought the simple question, “what’s going on?” could
pack so much punch?
• To mastering execution
• To driving strategy
• To answer that question, we must connect the C-suite to the ground
truth
• To do that, I have three recommendations
• Deploy conversation intelligence software
• Do third-party win/loss analysis
• Run an annual or event-driven market research study
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