Carly Pledge has led Sales Development and sales teams across CloudCall and Datamaran. In this conversation, she talks about what BDR culture actually teaches sales leaders, why the transition from top performer to manager is one of the most misunderstood moves in a commercial career, and how community can be one of the most powerful and most underused intelligence assets in a B2B sales motion.

What we cover:
- Why hustle culture in BDR teams produces skills that most AEs quietly discard — and why that is a mistake
- The transition from BDR to AE: what nobody tells you before you make it
- Psychological safety as the operating principle of high-performing sales cultures
- Building a sales motion in a market where the buyer's understanding of their own needs is continually evolving (Datamaran operates in sustainability data and ESG reporting)
- Why community is a commercial intelligence asset — and why most organisations listen too little and pitch too much inside theirs
- Rapid Fire: the tools, the myths, and the metric every revenue leader checks on a Monday morning

Carly also shares the most honest thing a sales leader can say: "I'm a better manager than I am a performer." It is worth hearing the argument she makes around it.

About Carly Pledge
Carly Pledge is Head of Sales at Datamaran, a sustainability intelligence platform. She previously led Business Development at CloudCall and has spent her career building and scaling commercial teams in B2B technology. She is a former colleague of Mike's from the CloudCall years.

Links:
The Outside Seat website: theoutsideseat.com
InsideNow: insidenow.io
Carly Pledge on LinkedIn: https://www.linkedin.com/in/carly-pledge/
Steve Myers (My Sales Coach): https://www.linkedin.com/in/stevemyers0/
Jacqueline de Gernier (GWI): https://www.linkedin.com/in/jacquidegernier/

The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week.

Episode 4 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a-sales-exec/

InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. http://insidenow.io

Stephen Jenkins is Regional VP at Glean, the enterprise AI knowledge platform that grew from $100m to $300m ARR in fifteen months. He covers everything outside the UK across the Nordics, Benelux, Southern Europe, and DACH, and co-founded Sales Heads, an invite-only community for senior sales leaders built around honesty and no bravado.

In this episode of The Outside Seat, Mike Tumalty and Stephen Jenkins cover what the enterprise AI buyer is actually asking in 2026, why Glean never brings the product into the first few conversations, what the Sales Heads Amsterdam roundtable revealed about AI and SDR engagement, and why Jim Collins' Good to Great still shapes how Stephen builds operating rhythms across twenty-plus markets.

What we cover:

• The shift in the enterprise AI buyer question: from "what is AI?" to "how do I unlock value without creating risk?"
• The blueprinting session: how Glean sells to non-technical buyers without leading with the product
• Why cold calling is not dead and what the Amsterdam Sales Heads roundtable revealed about AI outreach
• The dual perspective of selling AI while using AI to run the commercial operation
• Structure brings freedom: operating rhythm as the constant across twenty-plus markets and cultures
• Why Sales Heads was built: the loneliness of sales leadership and the silence problem
• Good to Great, pipeline generation, and the desire to be great

About Stephen Jenkins:

Stephen Jenkins is Regional VP at Glean and co-founder of Sales Heads. His career spans ServiceNow, Jamf, Miro, and Glean. He is based in the Netherlands.

LinkedIn: https://www.linkedin.com/in/stevejenkins14/

Episode 3 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a...

The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week.

InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io

Jim Misuraca has won Adobe Partner of the Year twice. He has spent 20 years building partner programmes across Fortune 500 and 10-person startups, mostly in MarTech, data and ad tech. In this episode he sits down with Mike Tumalty to talk about what genuinely separates the partnerships organisations that generate revenue from the ones that produce activity reports.

This is a conversation about the structural reasons partnerships is still misunderstood inside most B2B technology businesses, why the friction between direct sales and indirect motions is healthy when it is managed properly, and what hiring for a partner role actually requires when the traditional eight-years-in-vertical screen produces the wrong outcome. Jim is candid about where partnerships sits on the org chart, why it depends entirely on the type of partner you are, and what AI is and is not changing for the function right now.
What is covered:

• Why winning Partner of the Year twice comes down to executive sponsorship, product commitment and vertical focus, not relationships alone
• The structural reason most companies underfund partnerships and treat it as a problem to fix rather than an operating motion
• Where partnerships should sit on the org chart and why the answer depends on whether you are SI, services or ISV
• The friction between direct sellers and partner motions, and why the best reps understand pie expansion versus margin erosion
• Hiring for partnerships: the figured-it-out gene, why traditional vertical-experience screens get it wrong
• How AI is changing partner work today (efficiency) and where it has not arrived yet (the core motion)
• The EMEA versus North America buyer dynamic: consensus building versus strong-voice decision making
• Crossbeam as the single most useful tool in a partner leader's stack
  
  

About the guest:
Jim Misuraca is a strategic partnerships and corporate development leader with two Adobe Partner of the Year awards to his name. He has operated across the MarTech, data and ad tech space for 20 years, working with companies from Fortune 500 down to 10-person startups. He is currently based in Phoenix, Arizona.

About the host:
Mike Tumalty is the founder of InsideNow, a GTM diagnostic and commercial due diligence consultancy. He has 25 years of B2B SaaS experience across ServiceNow, Lokalise, Decibel/Medallia, and Panaya.

Episode 2 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a...

Listen on Spotify, Apple Podcasts, and Amazon Music. New episodes every Tuesday.
Connect with Jim Mirusaca: https://www.linkedin.com/in/jrmisuraca/
Connect with Mike Tumalty: linkedin.com/in/miketumalty
Follow The Outside Seat: linkedin.com/company/theoutsideseat

The Outside Seat is produced by InsideNow. Find more at insidenow.co.uk