『How the Deal was Done | Enterprise Sales Podcast』のカバーアート

How the Deal was Done | Enterprise Sales Podcast

How the Deal was Done | Enterprise Sales Podcast

著者： Matthew Klingner | Andrew Kappel
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How the Deal was Done: Fast-paced interviews with top sellers & leaders. Each week we sit down with the best enterprise sales executives and Founders to unpack transformational deals & discuss the mindsets, strategies, and actions of world class performers.Matthew Klingner | Andrew Kappel 経済学
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  • S2 Ep 13: Machiel Kunst, From Sales Leader to CEO of Europe's Largest AI & SaaS Recruitment Org

    S2 Ep 13: Machiel Kunst, From Sales Leader to CEO of Europe's Largest AI & SaaS Recruitment Org
    2026/09/08
    Machiel Kunst built one of Europe's most successful B2B SaaS and AI sales recruiting firms on a premise almost no one else was willing to act on: hire ex-sellers to recruit sellers. He went from number-one AE out of 65, to building teams of 40+, to co-founding Bluebird — now 35 people, offices in Amsterdam and Sydney, on track to be the largest recruitment firm in its niche in Europe by revenue this year.This episode covers the playbook behind Bluebird's growth — including a nine-month nurture campaign to Sequoia that landed a 16-AE placement mandate — and the decade-refined framework Machiel uses to qualify sales talent.Key QuotesOn why deep market knowledge beats raw sales talent:"I knew exactly what was going on with all of these organizations, the dynamics in the market. And then I stepped into an account executive role — and I think that really gave me a massive advantage."On booking his own cold meetings as CEO:"Literally today I booked two meetings with VCs cold. I booked three meetings with companies cold. It's a skill set you should never let go if you possess it."On the most underrated career mistake in B2B sales:"I sometimes wonder whether people are aware of how important it is to be able to assess whether a company is possible of going sky high — because simply the vast majority of companies don't."On AI creating genuine personal connection:"I got a meeting prep from Claude and it said they have this one-liner at the bottom of every email. It was an Enzo Ferrari quote — it probably means this person is a bit of a petrol head, so you could start the conversation with that. And I did, and it actually opened up the conversation really nicely."The Tactical BreakdownScore candidates on characteristics, not just competencies — Machiel adapted Mark Roberge's framework from The Sales Acceleration Formula, scoring candidates on coachability, curiosity, work ethic, and intelligence. He tracked each hire's actual performance against their score for years and continuously refined it.Separate three evaluation lenses — Characteristics (the scoring model), competencies (deal size, stakeholder level, industry), and cultural fit. Cultural fit is an art, competencies are a checklist — characteristics are where you differentiate.Run a nine-month nurture before asking for business — Machiel emailed Sequoia's head of talent monthly with company milestones for nine months before getting a referral. That referral turned into 16 AE placements in Germany.Engineer premium events to make BD easy — Bluebird runs dinners for 20 founders with Ottolenghi catering and Dermot Duggan (CEO coach of Klaviyo, Databricks, Grammarly) speaking. The event does the work; the team closes in the room.The Sales Acceleration Formula — Mark Roberge — data-driven hiring framework with scoreable candidate characteristics; the foundation of Bluebird's qualification modelFireflies — AI meeting recorder; transcripts feed automatically into Bluebird's CRM — fireflies.aiClaude — meeting prep, post-call follow-up, presentation building, cold outreach via Claude Cowork — claude.aiGlassdoor — recommended for vetting company culture before accepting a role — glassdoor.comRuben Hassid — LinkedIn creator focused on AI automation workflowsDermot Duggan — Founder of 10XCEO USA; CEO coach to Klaviyo, Databricks, GrammarlyZoe Jervier Hewitt — Former Head of Talent Acquisition, Sequoia CapitalUniversal Cultural End Index — Bluebird's internal framework defining the characteristics that make someone a fit for a specific company, built before any hiring beginsGiving an A — Annual team exercise: write a letter to yourself from year-end explaining why you earned a 10/10 — not based on hitting number, but on who you becameConnect with Machiel LinkedIn — Machiel Kunst, Co-Founder & CEO, Bluebird
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    1 時間 7 分
  • S2E12: Sarah Thomas, Closing The Biggest Deal in Company History

    S2E12: Sarah Thomas, Closing The Biggest Deal in Company History
    2026/06/03

    How the Deal Was Done | Sarah Thomas, Strategic AE at Verkada

    Sarah Thomas closed the biggest deal in Verkada history. 1,000 retail franchise locations, a skeptical new champion, a botched proof of concept, and a three-party sell across customer, integrator, and Verkada internally.

    The deal nearly died over a scope miscommunication that put her integrity on the line. She revived it by owning the mistake, renegotiating the structure, and rebuilding trust at every layer.

    In this episode:

    • How to run parallel prospecting threads across a channel deal
    • What to do when your pilot surfaces a broken promise
    • How to beat a cheaper competitor on total cost of ownership
    • Why selling year four matters more than winning year one
    • How to structure staggered licensing around implementation reality

    Key Quotes

    "The customer said we had communicated one thing in the sales process — and during the POC it looked different. My integrity was challenged. But we owned our part of it."

    "How do they trust us year two, year three, year four? Not just buying equipment — truly partnering."

    "Can you even spend this money? It's uncomfortable asking, but maybe not as soon as I should."

    Resources MentionedFanatical Prospecting — Jeb BlountGong — deal intelligence and call reviewGemini — prospecting and account research

    Connect with SarahLinkedIn: Sarah Thomas, Strategic Account Executive, Verkada

    How the Deal Was Done | Host: Matthew KlingnerFor senior AEs, founders, and GTM leaders who want to close bigger, more complex deals.
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    1 時間 5 分
  • S2E11: Philipp Klein: From Legal Threats to a $1M Win

    S2E11: Philipp Klein: From Legal Threats to a $1M Win
    2026/05/19

    How the Deal Was Done
    Episode: Philipp Klein, From Legal Threats to a $1M Win
    Guest: Philipp Klein, Enterprise Account Director Companies: Blinkist | CoachHub Industry: Learning & Development / HR Tech
    Episode Summary
    Philip Klein joined CoachHub as one of its first five employees in 2019. In this episode, he walks through one of the most dramatic enterprise deals in the company's history — a nearly seven-figure coaching platform sale to Booking.com that spanned two years, survived a legal threat, and navigated a global pandemic.
    Key Moments in the Deal
    1. The Lead Came from an SDR Philipp credits the shared-room culture of celebrating every small win as the foundation that made the deal possible. That buzz and collective energy often makes up for what early-stage teams lack in formal training.


    2. Qualifying for Transformation, Not Just Interest CoachHub's calendar was full of the wrong meetings — coaching enthusiasts who wanted to coach 10–15 people. Booking.com's team was different: they asked how CoachHub could scale and weren't scared of big numbers.


    3. Reframing the Demo Request Rather than handing over access to an immature product, Philipp asked prospects to articulate what they actually needed to evaluate. That unlocked 4–5 additional stakeholder meetings that competitors — who just sent the login — likely never got.


    4. The Legal Crisis Days after signing the pilot, Booking.com went dark, then sent a formal email threatening legal action over a data privacy dispute. Philip's response: mapped stakeholders on LinkedIn, escalated to senior management, and brought in the CEO and Chief Legal Officer to a recovery meeting. The CLO's command of data privacy law reestablished credibility and broke the impasse.


    5. COVID as an Unexpected Catalyst When the pandemic froze Booking.com's business, CoachHub kept dialing. They proposed a small global pilot — 15 senior decision-makers at HQ — to stay relevant and transition from vendor to strategic partner. When budgets unfroze, they were first in line.


    6. Closing the Big Deal By late 2020, the close was — in Philip's words — the easier part. Financial incentives pulled the deal from December to November, and implementation meetings were already in stakeholders' calendars before the signature. The deal closed itself through the gate they'd built.
    Quotable Moments



    "The signature is basically just a gate the customer has to go through. Otherwise they cannot get to the next room."
    "You don't build confidence from successes. You build it from a mixture of successes and failures."


    "The difficult groundwork is what we did before. The big close was actually the easier part."
    Resources & Links
    Connect with Philipp

    • LinkedIn: https://www.linkedin.com/in/philippklein/
    • Case study video: Search "CoachHub Booking.com" to see the video he negotiated into the contract


    How the Deal Was Done drops weekly. Subscribe wherever you listen to podcasts
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    1 時間 31 分
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