First big presentation panic and learning to present

Rachel Dines is a B2B Marketing expert and advisor to multiple SaaS platforms, where she provides her specialty in deep tech companies with sales-led go-to-market motions. Rachel also writes a SubStack newsletter called Tech Dropout. Previously, Rachel was VP of Product and Technical Marketing at Chronosphere and a Forrester industry analyst turned product marketing leader. Rachel joins co-hosts Craig Rosenberg and Matt Amundson for a raucous romp through the world of building analyst relationships as a new SaaS vendor, the problem with startups having too many use cases, and why your B2B startup’s first marketing hire should really be a product marketer.

Plus, Rachel reveals what happened when she gave a friend some less-than-amazing career advice.

Also, Craig reveals his fondness for a certain slightly disparaging epithet, Matt releases his pent-up rage, and Producer Sam vows to make certain edits to the episode. 

Critical Takeaways

• Building relationships with industry analysts at research firms, such as Gartner or Forrester, is only getting more important for B2B startups and scale ups. By the way, ‘building a relationship’ in this context is not code for just paying to play; we mean actually fostering real human connections with individual analysts, even before you think about paying a dime for a subscription for their firm.
• If you want your SaaS startup to show up in things like industry analyst reports and ‘magic quadrants’, start by finding and reviewing the evaluation criteria for those reports, which are publicly available. Bonus tip: try to get involved early when criteria are being set. 
• For the ‘self scout’ of your product against the analyst’s criteria, bring in a few PMs (Product Managers) and SEs (Sales Engineers) to help you do a brutally honest self‑assessment, find weak spots, and see what shifts can be made. SEs are great resources to bring in because they are hyper aware of the critical issues with their own product and can provide clear-eyed insights.
• Pick one use case, one ICP (Ideal Customer Profile), and one persona to focus your go-to-market strategy on. Trying to be all things to all customers from day one is a recipe for dilution of your brand and burnout. Choosing one target (even if it feels narrow or imperfect) lets you focus your go-to-market resources, refine messaging, and build momentum for your company.
• Your first marketing hire should be a Product Marketer, not a demand gen specialist. Startups need someone who can define and refine messaging, narrative, positioning, not just pushing leads to sales. Without a clean story, demand gen spends often under‑deliver.
• With analysts, frequent light engagements, such as updates about new clients, features, saas founders turning over data, build familiarity and trust. Much of what shows up later in evaluations or quotes starts with these small, consistent touchpoints.

Chapters

00:00 - Episode Preview

00:50 - Endearing Terms for The Wonderful People from Massachusetts

03:27 - Introducing Rachel Dines, Author & Go-To-Market Advisor (Plus, Former Forrester Analyst)

07:24 - A Quick Convo about Data Centers & The Mission Impossible Film Franchise

10:24 - Giving Your First Solo Presentation as an Analyst with a Heads Up

16:18 - Why Startups Need To Engage The Industry Analysts Early On

20:22 - How Startups Should Approach Their Initial Analyst Relations Strategy

29:35 - Matt Admits What Grinds His Gears

31:23 - What Early Stage Startups Can do to Become Number One in the Magic Quadrant

34:08 - Startups Should Start with One Segment, User, and Use Case

46:51 - Why Your First Marketing Hire Should be a Product Marketer

52:21 - Some not so great B2B Marketing career advice

Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/

Epic Quotes

• “Focus, in the Go-To-Market side especially, is always the greatest Achilles heel of so many startups” - Rachel Dines
• “Pick a lane and win” - Matt Amundson
• “I can be bought for tiramisu” - Rachel Dines

Connect with Rachel

• LinkedIn: https://www.linkedin.com/in/rdines/ 
• Substack: https://racheldines.substack.com/ 
• Website: https://www.racheldines.com/ 
• How I Hacked the Moon: https://a.co/d/eSYYRWG 

Shoutouts

• Scott Mersy: https://www.linkedin.com/in/smersy/ 
• Sam McKenna: https://www.linkedin.com/in/samsalesli/ 
• Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge 
• Mission: Impossible - Rogue Nation (Christopher McQuarrie, 2015)
• The Studio (Apple TV+)
• Last Week in AWS (Newsletter): https://www.lastweekinaws.com/ 
• Corey Quinn: https://www.linkedin.com/in/coquinn/ 
• Cursor
• Windsurf
• Lovable
• Chris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ 
• Snowflake
• Denise Persson: https://www.linkedin.com/in/denisepersson/ 

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