Finding Watering Holes and Showing Empathy

Scrappy targeting, small segments, and extreme empathy for the audience sit at the center of this conversation on Scrappy ABM. Host Mason Cosby sits down with Tyler Lessard, CMO at Technology Advice, to move from a broad “B2B marketing leaders or demand gen leaders” ICP to focused clusters of accounts where the team can win day after day.

ㅤ

Tyler walks through breaking a market into specific industry subsegments like cybersecurity software vendors and HR tech vendors, backing those choices with win rates, average deal size, and field-level sales feedback. The discussion follows how in-person activations at industry conferences, niche newsletters, and original buyer insights research become “reasons to reach out” for sales and SDR teams. Along the way, Mason and Tyler highlight small, specific ABM programs with one rep and a handful of target accounts, measuring success by whether the right people at the right accounts show up, engage, ask questions, and move into real conversations.

ㅤ

👤 Guest Bio

• Tyler Lessard is the CMO at Technology Advice, a marketing leader who has built ABM in a couple of different organizations and worked with clients that have ABM use cases. In his role as CMO at Technology Advice, he focuses on B2B software, working with segments like cybersecurity software vendors and HR tech vendors. Tyler has spent a lot of time as a head of marketing running different ABM programs, partnering with sales reps, CROs, and CEOs, and helping companies across the board activate their ABM programs by reaching audience members across an ecosystem.

ㅤ

📌 What We Cover

• Moving from a broad target market of “B2B marketing leaders or demand gen leaders” to specific industry subsegments inside B2B software.
• Using data on where you win—like cybersecurity software vendors and HR tech vendors—to pick two or three segments and identify the top accounts to start with.
• Bringing a focused ICP story to the CRO and CEO with clear context, tactics, and programs instead of just saying, “We want to focus here.”
• Getting buy-in from field-level sales reps by asking them to poke holes in the strategy, combining their anecdotal feedback with quantitative data.
• Building an efficiency story using win rates, average deal sizes, ACV, and the idea that “if we spend a dollar here, the ROI will be higher.”
• Finding channels that actually get in front of the right people when attention is harder than ever, including in-person activations and local events.
• Treating original thought leadership and primary research as genuine value, not “lipstick on a pig,” and using it as an anchor for ABM programs.
• Creating a micro program of “reasons to reach out” so marketing intentionally gives sales and SDRs multiple touchpoints tied to research, webinars, and events.
• Using an in-person happy hour at RSA as a scrappy way to meet marketing leaders from cybersecurity vendors without buying a big conference sponsorship.
• Thinking in terms of watering holes, niche influencers, and newsletters like The Hustle instead of only chasing massive reach.
• Building an annual buyer insights report from first-party data and survey-based data to become a trusted source of market and buyer trends.
• Slicing research by segments like SMB to run smaller, niche activations where even 5–20 of the right people is a clear win.
• Repurposing research into webinars, blog posts, social posts with infographic-style images, on-demand content, and PR-style outreach to other media and podcasts.
• Measuring ABM programs by asking, “Did we reach the right people?” and looking at who opened emails, engaged with content, attended webinars, and asked questions.
• Using a qualitative lens alongside downloads, registrants, and pipeline to diagnose issues in targeting, messaging, value, or brand awareness.
• Applying a simple framework around data, distribution, destination, and direction to understand when an activation works or breaks down.
• Starting ABM small and specific by partnering with a single sales rep like “Sarah” and two or three accounts with a clear commonality, such as financial services accounts.
• Embracing constraints so a small ABM program becomes a creative process instead of trying to “do it all” on day one.
• Keeping the number of accounts small so it is easier to stay close to the data and see when 10 people from one target account register for a webinar.

ㅤ

🔗 Resources Mentioned

• Technology Advice: Mentioned as the company where Tyler is CMO and as a partner that helps companies across the board activate their ABM programs by reaching audience members across an ecosystem.
• solutions.technologyadvice.com: The place Tyler points listeners to learn more about how Technology Advice helps companies activate their ABM programs.
• RSA Conference: The cybersecurity conference where Technology Advice hosted a marketers’ happy hour as an ancillary in-person activation to meet target accounts and build one-to-one relationships.
• The Hustle newsletter: A large newsletter example contrasted with more niche communities and newsletters for reaching specific audiences.
• LinkedIn: Called out as the best place to follow and connect with Tyler Lessard and as the platform where Mason Cosby invites conversations about ABM.
• Scrappy ABM: Visit for more ABM tips and strategies.
• Connect with Mason on LinkedIn for a conversation about ABM

ㅤ

If you enjoyed today’s episode and found valuable insights for your business, be sure to subscribe to the Scrappy ABM podcast for more expert discussions. Don’t forget to leave a review and share this episode with your team or fellow marketers!