The SaaS Sales Performance Podcast

Rachel Roberts is Chief Revenue Officer at Level Access, bringing deep leadership experience from global firms like Cisco, Adobe and high growth SaaS scaleups. With a proven record guiding organisations from tens of millions to enterprise scale, Rachel stands out for helping teams adapt and thrive through periods of major change. Her work covers industries from marketing technology to cybersecurity and always puts people at the centre of transformation. In this episode, Rachel explains how to bring teams with you when changing strategy, go to market or ways of working. She shares honest stories about what works and what fails and why process alone is never enough. You will learn why most teams resist change, how to unlock informal leaders and why trust is your most important asset in a transformation. Rachel reveals her approach for building buy in, using FOMO to drive new habits and setting a vision that stretches people but keeps them united. The conversation covers compensation mistakes, keeping teams productive through uncertainty and what to do when your first attempt does not land. There is advice for new CROs taking over in times of upheaval and guidance on setting a bold vision without losing clarity. 00:00:00 Welcome and Rachel’s journey from Cisco to Level Access 00:02:10 Lessons learned leading change at Adobe and cybersecurity firms 00:05:30 How to win hearts and minds before rolling out new ways of working 00:09:15 The role of informal leaders and McKinsey research on successful transformations 00:13:00 Building trust by owning mistakes and fixing compensation models 00:17:30 Creating regular listening forums and why small cohorts beat big town halls 00:21:00 Setting vision as an ongoing process and making sure it passes the 30-second test 00:25:10 Helping high performers rise to a challenge while supporting those who struggle 00:28:30 Advice for new CROs on balancing board demands and team needs 00:31:50 Navigating constant change in growth companies and timing transformation work 00:36:00 Final tips for resilient leadership and keeping teams together during turbulence

In this episode, Keith joins host Matt Milligan to unpack how he helped PandaDoc scale efficiently after pandemic hypergrowth, revamp its GTM strategy and 4x average selling price, all by doubling down on execution, team alignment, and ICP focus. Keith shares the radical mindset shift that enabled his team to stop chasing "ankle biter" deals and start prioritising the biggest opportunities. You’ll also learn how letting go of non-core use cases helped PandaDoc solidify its category dominance in sales and rev ops. This is a masterclass in sustainable scale, ownership culture, and resilient team building. 00:00:18 – Introduction: Keith Rabkin, CRO at PandaDoc, on Scaling High-Growth SaaS Teams 00:01:37 – PandaDoc’s Strategic Shift: From Sales Proposals to E-Signatures 00:02:25 – Sustainable Growth: How PandaDoc Quadrupled Average Selling Price (ASP) 00:03:30 – The Power of Focus: Prioritising High-Impact Deals Over "Ankle Biters" 00:04:40 – Mastering the ICP: Why Sales & RevOps Became PandaDoc’s Core Strength 00:05:42 – Building Resilient Teams: Keith's Approach to Tenacity, Ownership and Learning 00:07:48 – Leveraging Personal Resilience at Work: Connecting Life Experiences to Professional Growth 00:09:25 – The OWL Framework Explained: Empowering Sellers with Ownership, Wisdom, and Learning 00:11:47 – Cascading Ownership Culture: The Crucial Role of Frontline Leadership 00:13:01 – Flat Team Structures: Lessons from Google on Optimising Leadership Spans 00:14:34 – Strategic Talent Acquisition: Why Keith Personally Sources Talent on LinkedIn 00:16:00 – Contrarian Hiring: Seeking Candidates with Resilience and a "Chip on Their Shoulder" 00:17:44 – Inside Keith’s LinkedIn Strategy: Personalised Outreach for Top Talent 00:20:26 – The CRO's Role: Balancing Detail Orientation with Strategic Leadership (T-Shaped Model) 00:22:51 – Empowering vs. Micro-Managing: Navigating Leadership Dynamics with Frontline Managers 00:24:35 – Leading Through Change: Key Lessons from PandaDoc’s Transformation Journey 00:26:43 – Effective Learning in Sales Enablement: Customising Training to Individual Motivations 00:28:50 – Final Thoughts: Driving Team Success Through Ownership, Repetition and Transparency

Keenan is the celebrated author of the bestselling book "Gap Selling" and the CEO of A Sales Growth Company, providing transformative sales training and consulting for organisations worldwide. With a dynamic career journey—from dominating sales roles to becoming a globally recognised thought leader. Keenan brings unique insights into driving sales excellence through precise enablement and collaborative leadership. In this episode, host Matt Milligan sits down with Keenan to discuss how effective sales leaders diagnose and remove bottlenecks within their organisations. Keenan reveals why prioritisation, visibility, and cross-functional collaboration are critical to breaking down barriers and accelerating team performance. He also delves into one of the most pressing topics in enablement today: proving the ROI of your team's efforts. Listeners will learn actionable methods to measure and communicate the true impact of sales enablement programs, ensuring alignment, buy in, and sustained investment from leadership. 00:00 – Introduction & Theme 00:01:15 – Keenan’s Background & Journey into Sales 00:05:30 – Why CROs May Not Make the Best Authors 00:08:45 – Identifying & Removing Sales Bottlenecks 00:12:00 – Prioritising Cross-Functional Collaboration 00:15:20 – Creating Visibility & Transparency in Sales 00:18:10 – The Role of Enablement in Modern Sales Orgs 00:21:30 – Proving the Value of Sales Enablement 00:24:15 – The Future of Enablement & Skill Development 00:26:00 – Closing Thoughts & Contact

James Tudway is a Commercial Leader and Go To Market Strategist, currently Vice President of HG Insights, with deep expertise in leading revenue teams through product misalignment and market disruption. With years of experience scaling global sales organizations, including a recent stint in California. James returned to the UK to help turn around a SaaS data business grappling with churn, long sales cycles, and enablement blind spots. Known for building resilient GTM functions and high impact sales cultures, James brings a candid, pragmatic perspective to leadership during turbulent times. In this episode, host Matt Milligan and James discuss what it really takes to lead a sales team when your product is behind the curve. From introducing a “hero model” for performance to balancing budget between enablement and engineering, James offers tactical insights on coaching, morale, compensation, and retaining top talent when the odds are stacked against you. You’ll hear how fragmented development efforts can quietly erode renewal rates and how sales leaders can reframe the conversation internally to secure long term wins.00:00 – Introduction & Relocating Back from the U.S. 00:03:15 – Leading When Product Isn’t Ready 00:06:00 – Why Customers Pause: The Real Churn Drivers 00:08:00 – Facing the Hard Truth: Falling Behind Competitors 00:10:30 – The “Hero Model” Approach to GTM Talent 00:12:30 – Rebuilding Morale with Comp Structure & Focus 00:15:45 – How Enablement Gaps Undermine Performance 00:18:20 – Budget Prioritization: Product vs. People 00:21:00 – Advice for Vendors Navigating Budget Pushback 00:24:15 – Final Thoughts & Partnership Opportunities

Edmund Frey is a veteran revenue leader and former Chief Revenue Officer at Spryker, where he led global sales expansion and helped the company become a market leader. With 30+ years in enterprise sales at organisations like Oracle, Adobe, and SAP, Edmund now serves as Founder & Managing Partner of Edventure Capital, a go to market advisory and early stage investment firm. forming teams in today’s challenging market. In this episode, Edmund tackles this challenge head on, sharing 7 actionable strategies to accelerate sales rep ramp time and build a more resilient, high-performing sales team. He outlines how streamlining processes by 30% can shrink onboarding time by an equal 30% (and even cut failure rates by 50%) , and explains how focusing your existing talent on the right opportunities can drive 30 to 40% more sales with the same headcount . Edmund also offers a fresh perspective on targets, suggesting that giving top reps smaller quotas can sometimes yield better results than chasing ever increasing numbers, an approach aimed at sustaining team morale and success in tough times. Listeners will come away with a practical framework to maximize their sales team’s performance and morale, all while efficiently navigating the current economic headwinds. 00:00:00 Introduction – Meet Edmund Frey (ex-Spryker CRO) and overview of the episode’s theme. 00:03:15 Career Journey – From Adobe and SAP to scaling Spryker’s global sales organization. 00:07:30 Resilience & Productivity – Why modern B2B sales teams must do more with less. 00:10:45 Ramp Time as a Priority – Measuring ramp-up and accelerating new rep onboarding. 00:15:00 7 Principles for Efficient Ramp – Edmund’s framework for rapid sales team ramp-up. 00:18:20 Hiring Profile – Hiring reps with the right capabilities for your market. 00:20:10 Steady Onboarding – Avoiding the pitfalls of over-hiring and training overload. 00:22:00 Focusing Resources – Deploying your best reps on high-value deals and opportunities. 00:24:15 Smart Quota Setting – Setting fair, motivating targets from the start. 00:26:05 Communicating OKRs – Translating big objectives without overwhelming the team. 00:28:00 Twin Ramping – Pairing new hires with veteran mentors to speed up learning. 00:30:00 Process Improvement – Streamlining workflows to cut ramp time and errors. 00:33:00 Managing Change – Guiding veteran AEs when quotas suddenly increase (e.g. $2M to $5M). 00:36:00 Sales & Marketing Alignment – Holding marketing accountable to shared revenue goals. 00:38:00 “First 90 Days” – Edmund’s recommended onboarding playbook for new sales leaders. 00:40:00 Conclusion – Key takeaways and final advice for revenue leaders.