How I Hire

About How I Hire

Whispered Hiring - the podcast where we talk with senior GTM leaders about how they find, vet, attract and grow new talent.  Hosted by the team at Whispered, each episode uncovers the unwritten playbook for executive hiring that drives exponential growth.

Publisher

Whispered.com & Frontlines.io

Category

business

Language

en

Explicit

No

First episode

19 May 2025

Latest episode

3 Mar 2026

Latest episodes

38 episodes in the feed.

1. 

   3 Mar 2026

   Whispered Hiring with Jon Dick, CCO @ HubSpot

   In this episode of Whispered Hiring, Andy Mowat speaks with Jon Dick, Chief Customer Officer at HubSpot, about the hiring philosophy behind his decade-long rise from VP of Marketing to CCO. Jon's central argument cuts against conventional wisdom: stop searching for people who've seen the movie, and start finding people who can direct it. His frameworks for defining roles, evaluating AI capability, and onboarding senior leaders are specific, battle-tested, and immediately applicable. Topics discussed: Why "having seen the movie" is an increasingly hollow hiring signal. In a first-principles world, you don't need someone who's watched it before. You need someone who can direct it or star in it. Those are fundamentally different things from sitting in the audience. The most common exec hiring failure Jon sees: going to market before defining the non-negotiables. Writing a generic job description and planning to "calibrate through the process" is a recipe for shiny object syndrome and hires who were never set up to succeed. How HubSpot evolved its interview process over the last five to seven years to require every panelist to ask the same questions, enabling genuine cross-candidate calibration rather than a collection of disconnected impressions. Jon's "strong yes" standard for exec hires: if most of your panel comes back with a passing yes rather than a strong yes, you have a problem. Most interviewers lack the reps to take a firm stance and default to letting people through. A room full of soft yeses is a signal to stop, not proceed. Why Jon builds extended, unstructured time with exec candidates at the end of the final round, a practice borrowed from HubSpot's CMO Kip. A debrief dinner or afternoon whiteboard session isn't just better evaluation. It signals to the candidate exactly what kind of leader you'll be when things get hard six months in. Jon's two-part framework for evaluating AI capability: obsession with learning ("learn-it-alls" over "know-it-alls") and the ability to fly high and fly low, meaning a leader who can go genuinely deep on a workflow to actually implement AI, not just talk about it. His ultimate tell: how prepared a candidate is for the interview itself. If they don't show up knowing the basics about your business and role, they clearly aren't using the tools available to them. Why referencing starts inside the interview room. Jon's go-to question asks candidates directly what their back-channel references will reveal about their growth areas. The quality of that self-assessment is his most reliable indicator of self-awareness. How to close an exec candidate the right way: reflect back what you learned about them as a person throughout the process, in the offer structure, a thoughtful gift, or the closing conversation. Personalization at the finish line is the ultimate test of whether the hiring manager was actually paying attention. Yamini's onboarding practice for new senior leaders at HubSpot: before standard onboarding begins, the incoming exec spends several days with the core leadership team going deep on the business and each other. When HubSpot hired its Chief Sales Officer, it was five people for a couple of days. This replaces the "half-hour meeting shuffle" with the kind of depth that actually accelerates alignment and performance. ABOUT YOUR HOST: Andy Mowat (https://www.linkedin.com/in/amowat/) has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating. Learn more about about Whispered: www.whispered.com (https://www.whispered.com/) Interact with AI Andy: www.whispered.com/whisper-search (https://www.whispered.com/whisper-search)

2. 

   24 Feb 2026

   Whispered Hiring with Matt Martin, CEO @ Clockwise

   In this episode of Whispered Hiring, Andy Mowat speaks with Matt Martin (https://www.linkedin.com/in/voxmatt/), Co-Founder and CEO of Clockwise (https://www.getclockwise.com), about his contrarian approach to executive hiring that prioritizes immediate fit over long-term potential. Matt shares his tactical frameworks for structuring board involvement, selecting recruiting partners, and conducting first-call conversations that accelerate funnel velocity while maintaining rigorous standards. His insights reveal why predictability matters more than growth trajectory when hiring senior leaders. Topics discussed: Why Matt shifts executive candidates to text messaging as early as possible to break through the priority threshold and create fluid, responsive communication that email scheduling can't replicate, especially critical during closing stages when speed determines outcomes. The two-year hiring horizon framework: How simultaneously predicting company evolution AND candidate growth creates compounding uncertainty that destroys hiring accuracy, and why explicitly setting a two-year performance window (with anything beyond that as "gravy") establishes clearer mutual expectations from day one. The mechanics of board-led recruiting: Assigning one board member per executive search creates repeat-player dynamics with recruiting firms (VCs hire constantly, CEOs hire occasionally), provides horizontal industry pattern recognition, enables deeper network mining beyond first-degree connections, and delivers third-party validation during closing conversations. How recruiter selection should prioritize storytelling capability over brand reputation: Since recruiters conduct initial calls (not CEOs), their ability to authentically inhabit your narrative and explain your company's unique positioning becomes the primary filter, especially for complex PLG-to-enterprise or non-obvious business models. The selling-first philosophy for initial candidate calls: Using the product onboarding "calorie budget" concept to build candidate excitement before spending it down through a demanding process, with post-call enthusiasm serving as a legitimate qualification signal that saves time on misaligned candidates. Red flag signals that reveal fundamental misalignment: Candidates who allocate significant early conversation time to compensation discussions indicate mercenary motivation, while those who don't probe team composition, decision-making structures, or cross-functional dynamics demonstrate they don't understand how executive leverage actually compounds. The emergency-access expectation for direct reports: Why requiring cell phone access doesn't signal unhealthy always-on culture but rather creates a clear bright line for rare, genuine emergencies (website down, major customer issues, urgent board needs) that distinguishes serious executives from those who compartmentalize too rigidly. Cole Group's reputation advantage in GTM hiring: How the "name brand college effect" creates self-reinforcing talent access regardless of whether quality differences are objectively measurable, since top candidates make themselves available to perceived top-tier firms, giving those firms better candidate pools by definition. ABOUT YOUR HOST: Andy Mowat (https://www.linkedin.com/in/amowat/) has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating. Learn more about about Whispered: www.whispered.com (https://www.whispered.com/) Interact with AI Andy: www.whispered.com/whisper-search (https://www.whispered.com/whisper-search)

3. 

   17 Feb 2026

   Whispered Hiring with Paul Staelin @ 3 Time CCO

   In this episode, Andy Mowat speaks with Paul Staelin (https://www.linkedin.com/in/paulstaelin/), Fractional CCO at CornerstoneX and former CCO at Vercel, Trifacta, and Birst, about building customer success organizations that drove 40-point NDR improvements. Drawing from his Siebel Systems training and two decades scaling post-sales functions, Paul shares why CS teams fail without three distinct DNA profiles, his "time machine" question that exposes growth mindset, and how mental flexibility matters more than age when evaluating executives. Topics discussed: Why every customer touchpoint must deliver tangible value through discovery questions, teaching moments, or solution guidance rather than conversations about kids and dogs, treating customer experience as a scalable product where each step must justify its existence. The customer advisory board scarcity exercise: give customers exactly 5 votes to distribute across a six-month roadmap in any combination, forcing authentic prioritization beyond reactive fire drills while making customers co-owners of tradeoff decisions. Why high-performing CS organizations require three DNA profiles like chili ingredients: implementation veterans with project structuring instincts, sales-trained professionals comfortable with "golden silence" instead of filling awkward pauses, and former customers who provide authentic empathy for buyer challenges. How professional services implementations at Birst drove 40 percentage points higher NDR, and why "forward deployed engineering" is brilliant PS rebranding that risks creating unsustainable 3,000-person field organizations without deliberate customer ownership transfer strategies. The "time machine" question that reveals growth mindset: "if I gave you the grace of a time machine and you could go back and do this project again, what would you do differently?" separates introspective leaders from those who don't examine their approach. Why ageism concerns miss the real criterion of mental flexibility: will executives be guided by experience or led by it? When Paul was 35-year-old co-founder at Birst, he needed assurance executives wouldn't just "run a play" regardless of unique company context. Vercel's AI support training discipline under Matthew Sweeney: 30 support team members grading 5 AI responses weekly drove resolution rates from 30% to 70% over nine months, freeing engineers from repetitive tickets to focus on complex technical investigations. The executive onboarding principle that jamming managers in over team objections never works, requiring team excitement about candidates and designing roles with enough "real estate" so executives aren't crippled by dependencies on other functions. ABOUT YOUR HOST: Andy Mowat (https://www.linkedin.com/in/amowat/) has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating. Learn more about about Whispered: www.whispered.com (https://www.whispered.com/) Interact with AI Andy: (https://www.whispered.com/whisper-search)www.whispered.com/whisper-search (http://www.whispered.com/whisper-search)

Who has been a guest on How I Hire

Names identified in recent episode analyses. Showing up to five guests.

• Evan Huck
• Dustin Joost
• Ejieme Eromosele
• Tim Geisenheimer
• Karrie Sanderson

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

113,700

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

4 ratings

Podcast Authority Score: 56 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

66

Social presence

0

YouTube

82

Engagement

32