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SaaS GTM secrets unlocked for complex B2B sales, with Dave Boyce

19 Feb 26 | Written by Craig Taylor
In this episode of Truth, Lies & B2B Growth, Craig Taylor sits down with Dave Boyce, a SaaS builder, go-to-market (GTM) operator and long-time PLG advocate. Dave is also the author of Freemium. Together they unpack why SaaS has been forced to modernise GTM faster, and what B2B service firms selling complex deals can steal, adapt and apply right now.

(0:11) Craig: So welcome to the latest episode of Truth, Lies, and B2B Growth. We have a guest today and I'm delighted to be joined by Dave Boyce. Dave, welcome.

(0:21) Dave: Thank you so much, Craig. You mind if we just focus on mostly lies today?

(0:25) Craig: Yeah, that would be a very good start. Absolutely, yeah.  I mean, I've got to say, I've got on my screen sort of a list of your kind of focus areas in your profile. And, you know, you helped, what, build and sell seven SaaS businesses.

(0:41) Craig: You're an advisor to a number of scale-ups in the AI space.

(0:44) Craig: Correct me if I'm wrong on any of these points.

(0:46) Dave: Oh, this is correct, yeah.

(0:47) Craig: You're an investor, keynote speaker, a podcaster, exec chairman at Winning by Design.

(0:53) Craig: And I think you just launched a book, haven't you, Freemium?

(0:55) Craig: So I'm kind of thinking, what the hell am I doing with my time? How do you squeeze all that in?

(1:01) Dave: Secret, Craig, is to get old. That's what I've done.

(1:04) Craig: Yeah, well, yeah, tell me about it, yeah.

(1:07) Craig: So I think today it's going to be a really interesting conversation… (complex sales vs SaaS, sophistication, transition old to new).
(1:55) Craig: In 2025… trying to figure out what this new playbook would look like… and as we head into 2026… having to make it work.
(2:20) Craig: …where are we really? You’re across a lot of different companies… where we’re at.

(2:35) Dave: Yeah… all of it's changed. We are all to square zero right now…
(2:59) Dave: …anyone on LinkedIn who claims they have it figured out… probably… lying…
(3:20) Dave: …the ones who are actually succeeding are saying… we’re still experimenting.
(3:36) Dave: Two things… new generation of buyers… and AI changing everything.
(3:53) Dave: …Forrester… 70% of B2B buyers… millennials or Gen Z…
(4:28) Dave: …AI makes researching, comparing, trialing easier… upends selling and education.

(5:20) Craig: Do you think the biggest difference… is the desire to self-serve in the buying process?
(5:30) Dave: I do… self-service has been the trend all along… e-commerce… mobile… B2B SaaS… and now AI makes it easier.
(6:42) Dave: …buyers want to get their hands on it… not take the salesperson’s word for it…

(7:00) Craig: …Forrester also talk about… self-service increasing… buyers are invisible… sellers have lost control…
(7:30) Craig: …talk a little bit about freemium and product led growth…

(7:36) Dave: Freemium… give the base product away for free and charge for upgrades…
(7:47) Craig: …same way I interact with Spotify… Canva…
(7:56) Dave: …B2B: DocuSign, Dropbox, Twilio, Shopify… AI native: ChatGPT, Claude, Cursor, Mistral…
(8:19) Dave: …lowest friction… get someone into the ecosystem… expand usage and payment profile…
(8:54) Dave: …translate into complex sales… it’s happening there too.

(9:06) Craig: …system integrators… consultancies… reluctant to give away IP… now giving more away… diagnostics, assessments… baby steps…
(9:50) Craig: The role of the website's really changing as well…

(10:00) Dave: …conversion rates from clicks from LLM… higher intent… more traffic from LLMs… what is the website’s job now?
(10:26) Craig: …traffic tank from LLMs… zero click… but when people do reach your website, they’re further down the journey…
(11:10) Craig: …websites just aren't geared up to convert that later stage traffic…
(11:21) Dave: …I cut right over to an LLM… asks competitors, pricing… then I go back to the website when I’m ready…
(11:58) Dave: …how do we feed the LLMs… make sure they have what they need to help customers find us?

(12:05) Craig: AEO and GEO… optimizing for LLMs… tools… profile, how LLMs view your business…
(13:03) Craig: …LLMs, email, LinkedIn resurgence… less about gated content, more about high-intent signals…

(13:30) Dave: …LLMs get info from somewhere… does it come off my website or other sources?
(14:17) Craig: Both… optimize your site for discoverability… but trust comes from cross-references on authoritative sites…
(14:57) Dave: Like review sites?
(14:58) Craig: Yeah, exactly.
(15:31) Dave: …if I’m a marketer at day one… maybe I have catching up to do…
(15:42) Craig: …FOMO is rife…

(15:50) Craig: …how you architect all this… Clay rising… are you operating with Clay and tools like that?
(16:11) Dave: Yeah, for sure… launched agents… Clay + HubSpot + OneMind…
(16:29) Dave: …you gotta have a theory of the case… funnel… but Winning by Design tips it into a bow tie…
(17:40) Dave: …end of prospect journey is start of customer journey… impact, renew, expand… run experiments…
(18:38) Dave: …did it work? only if you measured conversion before/after… instrumentation is key…
(19:31) Craig: I love the bow tie model… advocacy/referrals often don’t exist in most companies…
(19:58) Dave: …open sourced it… basic framework is free to use…
(20:39) Dave: …advocacy loop: activate customers to bring new people into the left side of the bow tie…

(21:28) Craig: Dropbox referral loop… best example?
(21:41) Dave: Great example… but 15 years ago… many advocacy loops… especially in services… content, frameworks, benchmarks…
(23:10) Craig: …asset-based consulting… turning IP into tools…
(23:32) Dave: First principles of PLG: self-service… and generosity… empathy + generosity…
(24:46) Craig: Are they going to call you? Are they going to call me?
(24:48) Dave: They’re going to call me… generous give builds reciprocity…
(25:44) Craig: Hard for corporates to embrace.
(25:47) Dave: Super hard… defensive mindset leads to irrelevance… catch the wave… generosity early…

(26:59) Craig: …right-hand side of the bow tie… untapped area? quick wins?
(27:19) Dave: Indeed… expansion potential untapped… marketing should talk to existing customers too…
(28:22) Dave: …simple analog growth loop: get customers and prospects in the same room… dinner… workshop… they talk… trust loop closes…
(29:34) Craig: CEOs curl up at the thought… it’s their confidence in customer experience… worry customers won’t say nice things…
(29:57) Craig: …they doubt themselves whether their prospects… sorry, their customers are going—

(29:58) Dave: Two responses, I've seen that too. We live in the same world, obviously.
(30:03) Dave: “Oh no, no, I can't get my prospects in the receiving room as customers. They might hear terrible things.”
(30:10) Dave: Number one, then that's a truth… whether you're controlling the interaction or not… those opinions are out there… review sites… peer to peer… so go fix that.
(30:28) Dave: Number two, when we show up as humans… sponsored by our vendor… we don't say bad things about our host.
(30:50) Dave: …it doesn’t really materialize… in your living room… restaurant… club… they’ll tell you the bad things, but not a peer.

(31:09) Craig: It's a mindset shift… I remember the days of user groups… closed groups just for clients…
(31:20) Dave: Those can turn into gripe sessions.
(31:22) Craig: Yeah… hangover from those days… open floor to tell the vendor what you thought…
(31:34) Craig: …don’t hear of many user groups now… celebratory conferences… InBound…

(31:45) Dave: Interesting.

(31:47) Craig: At the top… you said you wanted to focus on some of the lies… we always ask guests… anything you’re hearing that’s complete bullshit?

(32:05) Dave: Two lies… opposite ends. One: “we just got to work harder or do more.” It’s not effort.
(32:20) Dave: …SaaS growth rates half what they were in 2022… paying 60% more per unit of growth… everyone’s trying.
(32:48) Dave: Second lie: “we have it figured out.” Playbooks that got us here will get us there… or we figured out the new playbook… I don’t think so.
(33:03) Dave: …need curiosity… architect a new way… figure it out before competitors…

(33:40) Craig: People will be reassured… making it work requires experimentation… blood, sweat, tears… clients want you to get it right first time…

(34:13) Craig: I recall a panel at Inbound… with AI, do we get to a point where go-to-market is completely automated… removing the human? Maybe in high-volume SaaS… but not complex sales…

(34:48) Dave: Are we de-laboring? Yes… handing tasks off to robots… like manufacturing… people click up… manage lines instead of stations.
(35:21) Dave: In go-to-market… automate the predictable… quotes, contracts… notes, summaries, configurations…
(35:38) Dave: But human element of complex selling won’t go away: fear, confidence, trust, stakeholder management, believability, ROI, internal approval…
(36:08) Dave: Humans click up… humanize the exceptional… robots take mundane predictable stuff.
(36:20) Dave: If I’m good at sales/marketing—hallelujah—strategic work. If you pride yourself on writing quotes… sorry, robot.

(36:46) Craig: And how do you figure that out? Look at the process end-to-end… where AI can step in.
(36:55) Dave: Indeed… map Bowtie data model… instrument stages… define processes inside stages… find robot-able steps… run experiments…
(37:43) Dave: …build a mathematical model… find highest leverage point (e.g., onboarding)… fix leaky funnel/retention… then come back to sourcing…

(38:17) Craig: You’ve got to start with the process, right?
(38:20) Dave: Start with the process, yeah.

(38:23) Craig: Great. I’m going to give you the chance to sum up… CEOs/CMOs listening… what 2–3 pieces of advice as we start the year?

(39:00) Dave: If I’m a CEO… think who in your market is most likely to change the game—probably smaller, nimble… add three years… ChatGPT launched three years ago…
(39:42) Dave: Give your innovative competitor three years… could they be the ChatGPT to your internet? Zoom to your GoToMeeting?
(40:10) Dave: McKinsey Three Horizons 70-20-10… don’t put zero in the 10% breakthrough bucket… carve out team, copy/paste what works… resource your future…
(41:00) Dave: …don’t end up with a perfectly efficient buggy whip factory…

(41:12) Craig: If wholesale change is needed… you need to go all in… people hold onto old models scared of losing revenue… world moves too fast…
(41:35) Dave: First one won’t work… in the 10% there’s failure, iteration… when it works, standardize, plug back in… permanent upgrades…

(41:58) Craig: Nice way to wrap up… where can people learn more?

(42:05) Dave: winningbydesign.com… free Growth Journal… LinkedIn… Substack: productledgtm.com… book Freemium… frameworks to experiment your way to greatness.

(42:47) Craig: I’ll be checking out Freemium… thanks for your time… real pleasure.
(42:55) Dave: Rock on, brother, thank you so much.

(42:58) Craig: Thanks for listening or watching… subscribe or leave a review… see you next time.

Things to look out for:

  • Why SaaS is ahead on modern GTM, and what is transferable to B2B complex sales
  • “Square zero” and how AI is changing discovery and decisioning
  • Self-serve in complex sales, what it really means in practice
  • The Bow-Tie model, and why post-sale is now a growth engine
  • Instrumentation and a GTM data model so experiments are measurable
  • How to run smarter tests, double down, and kill what is not working
  • Where authority now comes from, including third-party proof
  • “Generosity” that converts, using diagnostics, frameworks, and models
  • Advocacy loops that turn customers into pipeline
  • What to copy from SaaS, and what to ignore in complex B2B services
Written by
Craig Taylor
Co-Founder & Managing Director
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