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Sales Wisdom of Mark Cranney (podcast summaries)

December 31, 2025 Jeremey Donovan Leave a Comment

The Investor + Operator Podcast: How to Build a World-Class Revenue Org with Mark Cranney, Former a16z Partner (Nov 28, 2023)

  • When hiring an AE, I’m looking for success themes and progression
    • Intelligence (IQ & EQ)
    • Courage / Perseverance
    • Focus & Discipline
    • “Woo” – how they carry themselves; personality; ability to get attention
    • Ability to work in a team
    • Competitiveness
  • When hiring a head of sales, CEOs of early stage companies should look for candidates who have put together their own playbook rather than executing somebody else’s. So much also depends on alignment:
    • Motion: PLG; inbound/marketing-led; outbound sales-led (bottom up vs. top down); channel-led
    • Size: strategic; enterprise/majors; mid-market/commercial; SMB
    • Product complexity
    • Verticals
    • Competitive dynamics: greenfield; brownfield/knock-out
  • Also when assessing sales leaders
    • Are they a student of the game?
    • As a leader, do they have a following who will come with you to the next place?
  • “The value of a go-to-market organization is to help customers determine what their buying criteria is. It is not about communicating value; it is about creating value.”
  • In the first 90 days as a new CRO of a startup, run a bootcamp
    • Include everyone – sales, marketing, professional services, and CS
    • Delivered by the executive leadership team
    • 50% product
    • 50% process: Go through all the stages and gates of the sales process in case-study fashion using actual customer examples. Arm them with messaging & questions. Make them pitch-certify on each step.
    • Make bootcamp competitive and be prepared to exit people who do not meet standard
    • Bootcamp is also a forcing function to identify gaps in: strategy; content; roadmap; revtech; pricing & packaging
  • I want my SEs to be on par with a strong technical product manager

The Run Revenue Show: How to Navigate Downturns and Adapt to Market Changes with Mark Cranney, Go-to-Market Advisor (Aug 21, 2023)

  • You need to accurately forecast both good news and bad news
  • I’ve always operated with a rolling 5-quarter forecast
  • You should have executive sponsorship and activity on key deals
  • You have to be excellent at competing against ‘do nothing’
  • Book recommendation: Art of War

IoT Connect Podcast with Guest Mark Cranney (Oct 20, 2022)

(this was a conversation about SkyDio and drone applications)

The GTMnow Podcast: GTM1 – Creating a Winning Culture with Mark Cranney (Oct 18, 2022)

  • On talent
    • Track record of exceeding quotas (or being in competitive environments if coming right out of school)
    • Character – Focused/disciplined; “woo” to get people to rally around them
    • “Golden spur” = what is driving them to want to be successful
  • The people you hire need to want (opt-in) to work in the system and culture you have built
  • Ideal new hire bootcamp
    • 4 to 5 days, in-person
    • 50% product & market including: value proposition; segmentation/targeting; competitive differentiators; roadmap to close competitive product gaps; competitive playbooks to defeat incumbents, upstarts, and ‘do nothing’
    • 50% sales process – based of case studies with customers
    • Some people may not make it through bootcamp
  • Confidence comes from unconscious competence
  • ‘Executing a competitive strategy’ is a phase that comes before the ‘technical validation event’
  • It is our job in sales to teach prospects how to evaluate new technology.
  • PoCs/PoVs couple technical validation with ROI/business case
  • You have to get granular on the buying criteria at each of three levels: CxO, middle managers, and individual users.
  • “If you are not laying competitive traps, you are stepping in them.”
  • Highly competitive environments will look toxic to some people and look like heaven to others.
  • Be a student of the game – practice, drill, rehearse. It is what you are doing when no one is looking.

I’m Not Selling You Anything: Mark Cranney (Aug 10, 2022)

  • At PTC, you measured your time in quarters. There was high accountability.
  • When you speak with a gate keeper, just give your first name so they assume you are someone well known.
  • Competence -> confidence -> conviction -> courage

Legends of Sales & Marketing: Sales Legend Mark Cranney, Former COO of SkyDio (Sep 14, 2021)

  • PTC had to retool its GTM when transitioning from CAD/CAM to PLM.
  • “The two big drivers of value creation [during the sales process] are technical validation/POC and building the business case with ROI.
  • Why you over someone else is where the technical validation comes into play and the business case starts to form.
  • You need to understand the buying criteria of people at all 3 levels of the value pyramid:
    • CxOs: Focused on setting strategies, objectives, and initiatives. They determine ‘why do anything’ and later on ‘why now.’
    • VPs/Directors: Focused on achieving funded initiatives. They determine ‘why you’ via the PoC.
    • Individual contributors: Focused on using technology and process to fulfill the initiative.

Mission Daily: Running Your Business Like a Team Sport with Mark Cranney (Jun 20, 2019)

  • a16z Executive Briefing Program
    • Focus: G2000 and large government agencies
    • Roles: Mainly CIOs but sometimes other CxOs
    • Value Offered: “Curated Innovation” – Tell us about your initiatives and we will go inside or outside our portfolio to curate a list of companies to put 1:few in front of the executive
  • Selecting talent using success themes
    • Courage, focus, discipline, ‘woo’, what things they have had to overcome, where they are at in their life stage
    • junior military officers; team sport athletes

Sales Hacker Podcast: 21. The Making of a Top-Producing Silicon Valley VP of Sales w/Mark Cranney (Aug 22, 2018)

  • Talent:
    • Track record of past performance
    • Character: Courage; Competitiveness; Focus/Discipline/work ethic to get better on a day to day basis; Coachability; empathy; intellectual curiosity to figure things out
    • Golden spur = what motivates them
  • Example of courage: Overcoming resistance in a sale by going around or above
  • Competence gives you confidence which gives you courage
  • Hire for strengths since it is difficult to fix weaknesses
  • Criteria for a great startup CRO
    • Great recruiting eye
    • Have not merely executed by actually created a sales playbook for your GTM motion
  • Get very granular on actual AE productivity during ramp
  • It is a mistake outsource sales process design and enablement.

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