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Hello, I'm Kathleen.

Kathleen Randall is a rare "Venn diagram intersection" of technical knowledge, sales execution and strategic go-to-market experience. Kathleen has a reputation as a forward-thinking leader in the go-to-market (GTM) and sales advisory field. She has a domain expertise in governance, risk, compliance (GRC), audit, and cybersecurity solutions. With over 25 years of diverse experience, she has excelled in roles ranging from a Deloitte auditor, to a GTM strategist, with 20 years of operating experience as a seller and senior sales leader with a global impact. Kathleen is recognized for her expertise in navigating complex sales challenges developing effective GTM strategies, particularly with enterprise B2B SaaS software companies. Her impressive background includes operator and leadership contributions to startups (sub $5M ARR), as well as established companies such Deloitte, ServiceNow, Optiv (fka Accuvant) and Dell/RSA.

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My Story

They called me "GSD" (Getting S*** Done) for a reason. I thrive with passionate teams who value outcomes over titles and immediate paychecks. As the first-born of immigrant parents, I feel driven to create success that impacts generations.

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I love every aspect of sales—strategy, process, and closing deals. My background spans technical consulting, sales engineering, and leadership across companies of various sizes and growth stages.

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As I now work exclusively with B2B seed-stage startups as a go-to-market strategy advisor, I've witnessed innovative software companies struggle with sales pipeline creation and closing deals in today's AI-fueled marketplace. In this competitive landscape, FOUNDERS themselves become the true differentiator for a start-up in the early days.

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Great sellers aren't born—they're built through countless hours of craft refinement. Like physicians or engineers, top sales professionals require years of experience and diverse training. My journey from technical consultant to sales engineer to top-performing rep and sales VP has given me unique insights into what truly works in real life.

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I've created training programs and enabled hundreds of sales professionals across different organizations. Now, I'm channeling my passions for both sales coaching and early-stage B2B SaaS startups into this program—designed to be the 3rd leg of a winning go-to-market strategy's "stool" (e.g. product + marketing + sales) that results in igniting a startup's revenue growth journey.

Roger Thornton, 

Ballistic Ventures

“Kathleen is a secret weapon for cybersecurity startup founders. She brings deep sales expertise and has an extraordinary ability to coach founders—many of whom have little professional sales experience—into confident, capable sales leaders. I’ve seen firsthand how her work can accelerate founder-led sales and drive real traction. While engaged in founder led sales, it is critical to make the most of every intro. I recommend her without hesitation."

Reed Clayton,
2X Founder

"Working with Kathleen was a game-changer for our startup. Her personalized coaching and industry expertise propelled our go-to-market success."

75 Sales Reps' Survey Results

“Her training exceeded my expectations. Her valuable insights and practical tools has helped me put together a game plan to crush my number this year.”

Check out my podcast, The Go-to-Market Lab

The Go-to-Market Lab podcast is for founders and revenue leaders of pre-seed to growth stage tech B2B startups. Check it out on Spotify, Apple Music, and YouTube. 

Want to speak directly with your future Sales Coach, Kathleen Randall?

Interested in applying for the next cohort?  

 

Contact me here, or on LinkedIn: 

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© 2025 by Waypoint GTM Advisory L.L.C. 

 

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