Podcast Summary: Owning the Outcome – "AI, Sports, and Global Impact: The Engaging.io Story"

Podcast: Owning the Outcome
Host: Sarah McDevitt (HubSpot, Sr. Director of Partner Strategy)
Guest: Michelle O’Keefe (Co-founder and CEO, Engaging.io)
Date: August 21, 2025

Overview

This episode features Michelle O’Keefe, co-founder and CEO of Engaging.io, an Australian-based technical powerhouse and long-time HubSpot partner. The conversation unpacks Engaging.io’s bold leap into the North American professional sports market, their philosophy for building trust with complex clients, practical lessons on applying AI for businesses, and the value of community and candor in the HubSpot ecosystem. Michelle’s signature punk rock energy, radical honesty, and advocacy for openness and specialization anchor this deep-dive into the realities—and opportunities—of building a global agency in an AI-first era.

Key Discussion Points & Insights

1. The Engaging.io Backstory and Core Values

[01:28–02:13]

• Longevity and Experience: Engaging.io has been operating for 16 years (“agency years are like dog years”).
• High Technical Acumen: The agency is built on strong technical foundations, excelling in complex CRM integrations and custom work.
• People-First Culture: Michelle stresses that agency life demands a culture where people enjoy showing up:

  “It’s important to make sure that your people feel supported and that work is somewhere they like to spend their time.” (Michelle O’Keefe, 01:46)

2. Breaking Into North American Pro Sports

[02:13–04:15]

• No Accidents, Just Opportunity: Engaging.io’s move into the US sports market wasn't strategic at first. Their technical edge opened initial doors.
• Verticalization as a Growth Lever: While not necessary in APAC, Engaging.io deliberately specialized in sports for the US—also “killer case studies,” like work with an NBA team, became powerful social proof.

  “We decided to over-service them as much as was physically possible to make sure we had a very good case study.” (Michelle, 03:54)

3. Building Trust with Data-Sensitive Clients

[04:15–06:08]

• Trust is Table Stakes: Especially when dealing with fan and proprietary data of sports organizations.
• Transparency and Honest Conversations: Early alignment and forthright, even uncomfortable, conversations are critical for converting skeptics into advocates.

  “Uncomfortable conversations can actually lead to converting some people into advocates…” (Michelle, 05:50)

4. Specialization vs. Breadth (And the Real Engaging.io Niche)

[06:08–07:37]

• Beyond Sports: Though known in the US for sports, Engaging.io specializes in complex use cases across finance, SaaS, property, F&B, etc.
• Common Denominator: Complex technical and organizational problem-solving, not a single sector.

5. AI Adoption and Realities for Clients

[07:37–10:09]

• AI is Not a Magic Pill: Many businesses have misconceptions—hoping AI will fix all problems or save costs without foundation work.
• Criticality of Data Hygiene:

  “People need to clean their data… or else AI isn’t really… going to work.” (Michelle, 08:30)

• Internal AI Committee: Cross-functional team tests and vets AI tools—soon to be shared via a “no-bullshit” guide for others in the ecosystem.
• Emphasis on Guardrails: Stick with experiments long enough to judge, and focus on data security and process rigor.

6. Data Hygiene: The Painful But Crucial First Step

[10:09–11:24]

• Clients Often Underestimate the Work: Many either ignore cleaning or expect the agency to handle it entirely; the reality is it’s resource-intensive and sometimes only appreciated after a negative experience.

7. Internal Use of AI: Empowering, Not Replacing

[11:24–12:35]

• Open Dialogue Fosters Trust: O’Keefe is transparent with her team—AI is about removing drudgery, not eliminating jobs.

  “It’s more what’s it going to allow you to be able to do now that you couldn’t do yesterday?” (Michelle, 11:33)

• Human-Centric Augmentation: AI is about enabling better, faster human-to-human work—not replacing it.

8. Leadership, Advocacy & Authenticity

[12:35–14:17]

• Punk Rock Roots: Michelle’s ethos—help others find a voice and champion those underrepresented in tech and wider business.

  “If I can use that loudness to make things a little bit easier… or to get someone to think a little bit more inclusively, then I’m pretty comfortable with that.” (Michelle, 13:54)

9. AI Hype vs. Reality

[14:17–15:28]

• Not Magic, Not a Cure-All:

  “It’s not magic, and it’s not going to solve all your problems without you putting in any effort…” (Michelle, 14:29)

• Risks of Rushing In: Over-eager implementation or disregard for data rigor can have real, costly consequences.

10. Championing Community and “Partner Generosity”

[15:28–17:54]

• Collaboration is An Accelerant: Learning from the Shopify ecosystem, Michelle believes partner collaboration accelerates adoption and collective impact.
• Education Remains Essential: Helping each other and customers understand HubSpot’s progress beyond its early roots is a collective job:

  “The more we [partners] can do that together, the better implementations… the more people we can really get to understand how great the platform is, the more prospects for all of us.” (Michelle, 16:31)

• Support for New Partners: Overcoming isolation and sharing mistakes—especially with new entrants—builds a stronger ecosystem.

11. Program Wishlist: Transparency & Embracing Change

[17:54–19:24]

• Transparency from HubSpot is Key:

  “You have a decision to make, you get on board or you get off board. So I think that openness is just so important.” (Michelle, 18:30)

• Change is a Constant: Agency life in tech is dynamic by nature. Michelle values having channels for honest feedback, venting, and reality-checks.

12. Final Advice: Specialize and Say “No”

[19:47–21:02]

• Hardest Lesson for Partners: Learning to say no is critical to avoid overextension.
• Power of Focus:

  “Pick something that you are really good at… and follow that. Do one thing really well first…” (Michelle, 19:54)

• Case Studies Fuel Growth: Demonstrated expertise paves the way to future opportunities—start with your core strengths, build outwards.

Notable Quotes & Memorable Moments

• On Trust and Difficult Conversations:
  “Sometimes uncomfortable conversations can actually lead to, you know, converting some people into advocates and believers that possibly weren’t before.”
  — Michelle O’Keefe, 05:50

• On AI Hype:
  “It’s not magic, and it’s not going to solve all your problems without you putting in any effort to those problems.”
  — Michelle, 14:29

• On Partner Collaboration:
  “Partners working together can be super powerful… the more we can do that together, the better implementations of HubSpot we can do, the better case studies, the more people we can really get to understand how great the platform is…”
  — Michelle, 16:31

• On Specialization:
  “Pick something that you are really good at… and follow that. Do one thing really well first... that gives you… the demonstrated experience and case studies which is going to help you win the next one.”
  — Michelle, 19:54

Timestamps for Important Segments

• 01:28 — Michelle’s “Three Points” on Engaging.io’s Identity
• 02:50 — How Engaging.io entered North American pro sports
• 04:38 — Building trust with sports teams and key customers
• 07:56 — What clients really want and misunderstand about AI
• 08:30 — Internal AI committee & “no-bullshit” guide initiative
• 10:09 — Most common data hygiene issues and client pushback
• 11:24 — How Engaging.io is fostering internal AI growth
• 12:56 — Michelle’s leadership roots and advocacy philosophy
• 14:29 — The truth about AI hype and risks
• 15:57 — The value of partner generosity and collaboration
• 17:58 — Desired evolutions in the HubSpot partner program
• 19:47 — Advice for partners: the power of saying “no” and focusing

Tone & Takeaways

The episode is candid, energetic, and packed with hard-earned lessons. Michelle challenges both partners and customers to face uncomfortable truths—about specialization, about data hygiene, about AI—and to step up to real collaboration. Her no-nonsense attitude blends with warmth and generosity—an open call for partners to build together for everyone’s benefit, not just their own.

For partners and listeners:

• Don’t chase every opportunity—focus.
• Build trust through honesty, especially in complex, high-stakes relationships.
• Take AI seriously, but don’t believe the hype—clean data is crucial.
• Leverage the support, candor, and collaboration found in the HubSpot community.

This summary captures the insights, color, and actionable wisdom of Michelle O’Keefe’s journey as shared on “Owning the Outcome.”