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Paul Williams: SMB vs. Enterprise Sales — The Playbook for Scaling Up

What really changes when an organization scales from SMB to enterprise?

In episode 2 of #GrowthDecoded, Paul Williams, Head of Enterprise Strategy & Planning Solutions Sales, joins MarketStar’s COO, Paul Grant, to break down the realities of moving upmarket — from structural differences in buying cycles to the mindset shifts that make enterprise growth repeatable and scalable. 

Join Paul as he dives into how enterprise sales demands stronger value proof, better organizational alignment, and a fundamentally new way of engaging customers. This episode reveals what signals indicate it’s time to move upmarket and how to stay outcome-first at every stage of the enterprise journey. 

 

Highlights of the Interview


Enterprise Selling Is a Different Motion Compared to SMB 
SMB motions can’t simply scale upward — the alignment, dynamics, and engagement required are fundamentally different. 

Customer Expectations Often Drive the Move Upmarket 
As companies scale, leaders at higher levels face different challenges and needs — naturally pulling sales conversations into enterprise motions. 

Enterprise Execution Runs on Proof and Readiness 
Sellers must meet customers where they are, validate readiness early, and align people, process, and technology across long buying cycles. 

Leadership Mindset Matters More Than Ever 
Enterprise growth demands a cultural shift: encouraging transparency, staying close to customers, and embracing a learn-it-all mindset. 

AI Is Raising the Bar for Buyer Expectations 
AI is accelerating how quickly buyers expect sellers to deliver outcomes, leaving sales teams in need of sharper intelligence to keep pace. 

About the Speakers

Paul Grant 
Chief Operating Officer, MarketStar 
Paul oversees global client delivery, technology, and operational execution at MarketStar, bringing with him decades of experience scaling global revenue organizations.

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Paul Williams
Head of Enterprise Strategy & Planning Solutions Sales, Atlassian  
Paul leads enterprise strategy and sales execution at Atlassian, helping enterprises align planning, execution, and outcomes as they navigate complex environments.

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Company

Atlassian is a global software company powering collaboration, productivity, and mission-critical workflows for millions of users worldwide. Its product suite—including Jira, Confluence, Trello, Bitbucket, and Compass—enables teams to plan, track, and support work across IT, operations, and business functions. 

With more than 260,000 customers, Atlassian helps organizations improve visibility, boost cross-functional alignment, and fuel delivery at scale. From fast-growing startups to the world’s largest enterprises, teams rely on Atlassian to modernize workflows and drive measurable impact.

www.atlassian.com

Industry
Software Development
Headquarters
Sydney, Australia (Global HQ) San Francisco, California (US HQ)