New episode on the Vibescaling Podcast, Mike Donohue! Been awesome doing these and have so many in the hopper (see below) - thank you all for the kind words and support so far.
Some of our previous guests:
Todd Busler, CEO @ Champify - see writeup here
Raphael Parker, CRO @ Mandolin (former founding GTM hire @ Segment) - see writeup here
Kyle Parrish, former VP of Sales @ Figma, see article here
Liam Mulcahy, GTM operating partner @ Kleiner Perkins, see article here
Pat Forquer, CRO @ Legora, see article here
Some of our future guests for Season One:
Jack Gashi, VP of Sales @ Avoca (recorded, in edits now)
Tomer Chernia, VP of GTM @ Cursor (recorded, in edits now)
Eleanor Dorfman, Head of Sales @ Anthropic (recorded, in edits now)
Kyle Norton, CRO @ Owner.com
Jason Gelman, Operating Partner @ Primary Ventures
Evan Cassidy, VP of Sales @ Decagon
Ghazi Masood, CRO @ Replit
Liam Mulcahy is coming on again!
Mike Heller, Partner @ Floodgate (former Dropbox & Clearbit GTM)
Rob Saliterman, VP of Sales @ Harvey
& others from our portfolio companies @ vibescaling
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM on LI or reply to this email. We’ll keep openings rolling and be super open to suggestions for similar guests.
We film in-person in SF & NYC at legit podcast studios and have hired a new post-production agency, so the quality will be high.
And now, onto the episode 🎙️
Links To Sections
VibeScaling Episode 6: Mike Donohue
Mike heads up sales at one of the leading AI customer support tech platforms right now, Maven AGI.
They’re an up-and-comer behind the behemoths of Sierra and Decagon - so it was interesting to hear how they’re thinking about the market.
I had Mike on my list for a while, especially after hearing him and Kyle Norton jam out on the Revenue Leadership Podcast.
A fellow Columbia grad &/ Northeast guy, was genuinely one of the nicer folks I interviewed on the show.
Mike’s Background
Mike Donohue is the CRO at Maven AGI, one of the fastest-growing AI agent companies focused on customer support automation.
Before Maven, Mike was SVP of Sales at Gubshup, a messaging AI tool, and spent time at PayPal to give BigCo a spin.
He was an early sales hire at Lean Plum, growing with the company from Series A through Series D and competing head-to-head with Braze during the mobile marketing wars.
Mike's career started unconventionally - while captain of the varsity heavyweight rowing team at Columbia, he ran a dorm business doing room cleaning, dry cleaning, and beverage delivery.
He started using Square to process payments, fell in love with the product, and eventually got hired directly by Jack Dorsey when the company was sub-100 employees.
He's a Philly native who will tell you Tony Luke's beats Pat & Geno's as the best cheesesteak in Philly.
Interesting Takeaways
"Sales is a science, not an art." Ask Mike 15 years ago, and he'd say sales was pure artistry - creative magicians closing deals. Now? He'd rather hire A and B players with an incredible playbook than try to scale 100 artists. Being prescriptive about activities, gives, gets, and resources at each stage is a lot more repeatable.
The interview question that separates good from great. Mike asks every candidate: "How do you leverage AI in your current job?" The meh answer is "I used ChatGPT to prepare for this interview." Good to great answers sound like: "I vibe coded 80% of my outbound messaging in Windsurf" - candidates actually building and automating their workflow, not just using AI as a research assistant.
The athlete mentality in sales: "The score takes care of itself." As a former national-level rower and captain of Columbia's varsity heavyweight team, Mike applies the same discipline to revenue. Focus on the inputs and the process - the results are a byproduct.
Where AI agents are actually working. Maven AGI is focused on customer support automation, where the ROI is obvious in 30 seconds - measurable deflection and resolution rates that buyers can validate immediately.
The Braze vs. Lean Plum horse race. Mike had a front-row seat to one of the great SaaS battles. His takeaway? Braze won by focusing on high-SMB and mid-market with a strong land-and-expand pricing strategy. That segmentation gave them a compounding advantage.
Sales dinners are dead. The old playbook of expensive dinners and face time doesn't convert like it used to. Buyers now expect sellers to be consultative educators - especially in AI, where executives want someone to explain what an agent actually is and whether it applies to them.
Level up your AI game or get left behind. The best salespeople are using Claude for writing because you can control the prompt and the project. Mike encourages his team to always be trying different AI tools - the cost of one not working out is far outweighed by finding the one that enables crazy scale.
Discussed In This Episode
Why sales is a science, not an art - and why hiring "artists" at scale doesn't work
The interview question that reveals how candidates actually use AI: meh, good, and great answers
How Mike went from running a dorm business at Columbia to getting hired by Jack Dorsey at Square
The athlete mentality in sales and why "the score takes care of itself"
Where AI agents are actually delivering ROI in customer support today
The Braze vs. Lean Plum horse race: what competing from Series A to C taught him about GTM
Why sales dinners are dead and education-first selling is the new playbook
How to stand out when reaching out for a job (hint: it's not just a LinkedIn DM)
Why the best salespeople are building with AI tools like Claude and Windsurf, not just using ChatGPT for interview prep
Timestamps
00:00 Intro & Best Philly Cheesesteak: Why Tony Luke's Beats Pat & Geno's
04:00 Running a Dorm Business at Columbia & Discovering Square
08:00 Getting Hired by Jack Dorsey When Square Was Sub-100 Employees
12:00 The Athlete Mentality in Sales: "Score Takes Care of Itself"
18:00 Why Sales is a Science, Not an Art - Playbooks Beat Artists
24:00 How to Evaluate AI Usage in Sales Interviews: Meh, Good & Great Answers
30:00 "I Vibe Coded 80% of My Outbound in Windsurf" - What Impresses Hiring Managers
38:00 Where AI Agents Are Actually Working in Customer Support
45:00 The Braze vs Lean Plum Horse Race: Competing from Series A to C
52:00 Why Sales Dinners Are Dead & Education-First Selling is Winning
58:00 Maven AGI is Hiring - What Mike Looks For in Candidates
Thanks for reading!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, partner @ Vibescaling - a GTM advisory, recruiting, media, and investing firm, working with seed through series C AI-natives to help them grow.
Where to find Vibescaling:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LI.
🫡 cheers,
Chris