The SaaS Sales Performance Podcast

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B2B SaaS sales are changing in real-time, and conventional wisdom is becoming quickly obsolete. On the SaaS sales performance podcast, we’ll provide you with the practical tools you need to take advantage of this rapidly changing environment. We read the latest research so you don’t have to. Our masterclasses are distilled down into indispensable practical advice, and we speak to the experts on the front-lines. This is the podcast for anybody wanting to be on the cutting edge of SaaS sales.

  1. How this viral AI company is reinventing roleplay practice

    1 NGÀY TRƯỚC

    How this viral AI company is reinventing roleplay practice

    Engineer-turned-founder Sriharsha “Sai” Guduguntla, CEO of Hyperbound, joins the SaaS Sales Performance Podcast to unpack how voice AI roleplay is reshaping sales enablement. We cover de-risking AI initiatives, why practice beats pipeline obsession, and why the top reps are the hungriest users of coaching tech. Plus: the wild go-to-market behind Hyperbound’s viral launch and what the future holds for enablement teams. In this episode, Matt sits down with Sai Guduguntla, co-founder & CEO at Hyperbound, an AI platform that lets enterprise sales teams practise real conversations through intelligent voice roleplay and coaching. Sai shares the founder journey from YC acceptance to a hard pivot, why “inbox-only selling” is fading, and how reinforcement—not one-off training—wins. You’ll learn: The research sprint behind Hyperbound: 25k LinkedIn messages, 10k cold emails, 2k user interviews Why Hyperbound pivoted from AI SDR to AI coaching—and why realism is everything How to de-risk AI in GTM (start with the problem, not the tool) The enablement reboot: reinforcement, measurement, and coordination at scale Why top reps adopt practice tools fastest—and how laggards get found out Tech notes: going from 15s latency to ~800ms; voice first, avatars later 00:00 — Intro: Welcome & guest setup (Sai, CEO & co-founder, Hyperbound)01:20 — Founder Journey: Engineer → Salesforce → 20-month build; YC entry; 17+ ideas07:00 — The Pivot: CROs react to AI roleplay; moving from AI SDR to enablement10:30 — Viral Traction: Launch (22 Jan 2024), influencer wave, fully inbound growth13:00 — YC & Conviction: Why YC backed the team over any single idea14:30 — AI in GTM: Signal orchestration, account research, AI coaching at scale17:00 — De-risking AI: Start with the business problem, not the shiny tool20:00 — Change Management: Why enterprise; accelerating rollouts with AI22:00 — Sellers & Tech: Curiosity vs ROI; looking beyond “more pipeline”25:00 — Practice Works: A-players use it most; turning Cs into As with reinforcement28:00 — Enablement 2.0: From events to ongoing reinforcement & measurement31:00 — Mediums & UX: Voice AI today; avatars/AR/VR when realism arrives33:30 — Latency Leap: 15s → ~0.8s responses; what the next year could bring36:00 — Closer: Are great sellers made or born? (Made.)

    35 phút
  2. Why Revenue Leaders are not Teachers and how AI is reimagining the sales profession

    3 NGÀY TRƯỚC

    Why Revenue Leaders are not Teachers and how AI is reimagining the sales profession

    In this episode of the SaaS Sales Performance Podcast, host Matt Milligan is joined by Raouf Mhenni, Chief Commercial Officer at Sopra Banking Software (SBS). Ralph brings 25+ years of commercial leadership experience and shares powerful, actionable insights from his global career in sales, marketing, and product strategy. Introduction & Guest Background (0:00 - 1:20) Raouf shares his journey from pre-sales to sales leadership, highlighting his passion for customer interaction and continuous learning, especially in banking. Overview of SBS and Market Context (1:20 - 2:40) SBS provides core banking and digital banking solutions across Europe and North America, focusing on retail banking and specialized finance. Building Resilient & Productive Teams (2:40 - 4:50) Raouf emphasizes the fundamentals of hiring, onboarding, and engagement—adapting these processes for today’s talent market and technological environment. Evolving Recruitment & Onboarding (4:50 - 8:20) Shift from traditional hiring and onboarding to digital tools, e-learning, and leveraging internal referrals to attract motivated talent; importance of meeting with product teams and creating a sense of safety. Motivating Salespeople Beyond Money (8:20 - 10:50) Focus on learning, joy, and career growth, including aspirational paths to leadership, to retain top talent and foster engagement. Fostering Team Solidarity & Collaboration (10:50 - 14:00) Encourages creating spaces for sales teams to share experiences, work together on win-loss analyses without managers, and build peer leadership. Leadership During Tough Moments (14:00 - 16:20) Leaders should actively support and reassure their teams during challenging times through one-on-one conversations and human connection. Impact of AI & Digital Transformation (16:20 - 23:00) Raouf discusses AI's transformative potential across marketing, sales, and customer insights—speeding up processes, reducing time-to-market, and enabling smarter decision-making. Emphasizes the importance of change management and human-AI balance. Human Element & Balance (23:00 - 24:30) Despite technological advances, Ralph underscores the need to prioritize human connection, interaction, and wellbeing in the workplace. Closing & Contact (24:30 - End) Raouf invites listeners to connect via LinkedIn, emphasizing ongoing learning and adaptation in sales.

    34 phút
  3. Hungry, Humble, Smart: Building High-Performance Sales Teams with 25-year CRO Jamie Lee

    23 THG 8

    Hungry, Humble, Smart: Building High-Performance Sales Teams with 25-year CRO Jamie Lee

    Jamie Lee, seasoned revenue leader with over 25 years of sales and go-to-market experience, including roles as Chief Revenue Officer at Zesty and multiple GTM leadership positions. In this episode, Jamie Lee shares insights on navigating sales transformation, the importance of coaching, trust, and clear communication in sales teams, and how leaders can foster a growth mindset. He emphasizes the significance of foundational practices like OKRs, effective hiring based on humility, hunger, and smartness (EQ), and the critical role of leadership in developing high-performing teams. J amie also discusses overcoming resistance to new technologies, the importance of time management for leaders, and the value of continuous learning. He advocates for leaders to lead by example, prioritize coaching, and build a culture of self-awareness and humility to drive sustainable growth Introduction & Guest Background (0:00 - 0:09) Jamie Lee discusses his extensive sales and GTM leadership experience, including roles at Zesty and multiple CRO positions. Market Trends & Challenges (1:00 - 1:13) Insights on current market transformation, especially amid rapid AI growth and shifting team strategies. What Reps Seek in Roles (3:52 - 4:04) Coaching, trust, and clear communication are top priorities for high-performing salespeople. Embracing New Technologies & Growth Mindset (4:12 - 5:30) The importance of leaders modeling learning, supporting development, and fostering a growth mindset. Handling Resistance to AI & Change (6:07 - 8:06) Strategies for coaching team members hesitant to adopt new tools, emphasizing understanding motivations and fixed vs. growth mindsets. Leadership & Coaching Time Management (12:47 - 15:18) Overcoming excuses for lack of coaching; leaders should dedicate time to develop their teams and focus on hiring for humility, hunger, and EQ. Setting Effective Goals & OKRs (16:00 - 18:01) Using OKRs to align team efforts, focusing on inputs and actions that drive outcomes, and involving teams in goal-setting. Hiring with the Right Traits (21:36 - 25:54) Assessing candidates for humility, hunger, and smartness (EQ); practical interview questions and evaluation techniques. Building a Culture of Continuous Improvement (28:45 - 29:23) Jamie encourages ongoing learning, coaching, and community support to elevate the sales profession.

    34 phút
  4. The Importance Of OKRs In Your First 100 Days and Beyond Leading A PE-backed GTM Organisation

    19 THG 8

    The Importance Of OKRs In Your First 100 Days and Beyond Leading A PE-backed GTM Organisation

    In this insightful Podcast, Daniel Cummings, Chief Commercial Officer at PrecisionAQ, shares insights on leading a PE-backed GTM organisation through its first 100 days and beyond. He emphasises the importance of relentless execution, focusing on doing the work daily, and maintaining a "day one" mindset. Dan highlights the significance of clear goal-setting using OKRs, establishing strategic boulders, and maintaining transparency with dashboards that track progress. Daniel highlights the significance of clear goal-setting using OKRs, establishing strategic boulders, and maintaining transparency with dashboards that track progress. He discusses how to unify teams in a private equity environment by leveraging data, incentives, and a matrix organisational model that balances delivery and growth initiatives. Building a strong talent foundation and fostering a culture of continuous communication are also key themes. He stresses that the integration of AI into the go-to-market strategy, advocating for a people-centric approach to AI adoption, involving training teams to use AI tools effectively, and focusing on content creation and business insights. He advises managing team fears around AI by demonstrating its value and embedding it into daily workflows. Finally, Daniel underscores the importance of aligning with the board through consistent OKR reporting, presenting clear narratives, and setting strategic priorities to ensure sustained growth. 0:00 - 1:14 Introduction & Guest Overview 1:14 - 6:17 First 100 Days Focus 6:17 - 12:13 Building a Unified GTM & Talent 12:13 - 14:00 OKRs & Board Communication 7:12 - 10:17 Private Equity Context & Acquisition Journey 15:22 - 17:50 Team Structure & Collaboration 25:12 - 29:01 AI Strategy & Modern GTM 29:01 - 33:34 Managing AI Adoption & Team Fears

    34 phút
  5. How This CRO Went from $50 to $250 Million ARR

    12 THG 6

    How This CRO Went from $50 to $250 Million ARR

    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 Access00:02:10 Lessons learned leading change at Adobe and cybersecurity firms00:05:30 How to win hearts and minds before rolling out new ways of working00:09:15 The role of informal leaders and McKinsey research on successful transformations00:13:00 Building trust by owning mistakes and fixing compensation models00:17:30 Creating regular listening forums and why small cohorts beat big town halls00:21:00 Setting vision as an ongoing process and making sure it passes the 30-second test00:25:10 Helping high performers rise to a challenge while supporting those who struggle00:28:30 Advice for new CROs on balancing board demands and team needs00:31:50 Navigating constant change in growth companies and timing transformation work00:36:00 Final tips for resilient leadership and keeping teams together during turbulence

    27 phút
  6. How PandaDoc's CRO Keith Rabkin 4x Their Teams Average Selling Price

    23 THG 5

    How PandaDoc's CRO Keith Rabkin 4x Their Teams Average Selling Price

    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 Teams00:01:37 – 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 Strength00:05:42 – Building Resilient Teams: Keith's Approach to Tenacity, Ownership and Learning00:07:48 – Leveraging Personal Resilience at Work: Connecting Life Experiences to Professional Growth00:09:25 – The OWL Framework Explained: Empowering Sellers with Ownership, Wisdom, and Learning00:11:47 – Cascading Ownership Culture: The Crucial Role of Frontline Leadership00:13:01 – Flat Team Structures: Lessons from Google on Optimising Leadership Spans00:14:34 – Strategic Talent Acquisition: Why Keith Personally Sources Talent on LinkedIn00:16:00 – Contrarian Hiring: Seeking Candidates with Resilience and a "Chip on Their Shoulder"00:17:44 – Inside Keith’s LinkedIn Strategy: Personalised Outreach for Top Talent00:20:26 – 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 Managers00:24:35 – Leading Through Change: Key Lessons from PandaDoc’s Transformation Journey00:26:43 – Effective Learning in Sales Enablement: Customising Training to Individual Motivations00:28:50 – Final Thoughts: Driving Team Success Through Ownership, Repetition and Transparency

    31 phút
  7. Gap Selling Author, Keenan Reveals Why Your Sales Enablement is Broken

    13 THG 5

    Gap Selling Author, Keenan Reveals Why Your Sales Enablement is Broken

    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 & Theme00:01:15 – Keenan’s Background & Journey into Sales00:05:30 – Why CROs May Not Make the Best Authors00:08:45 – Identifying & Removing Sales Bottlenecks00:12:00 – Prioritising Cross-Functional Collaboration00:15:20 – Creating Visibility & Transparency in Sales00:18:10 – The Role of Enablement in Modern Sales Orgs00:21:30 – Proving the Value of Sales Enablement00:24:15 – The Future of Enablement & Skill Development00:26:00 – Closing Thoughts & Contact

    39 phút
  8. How the VP of Growth at HG Insights Turned Product Gaps into Sales Wins

    9 THG 5

    How the VP of Growth at HG Insights Turned Product Gaps into Sales Wins

    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 Ready00:06:00 – Why Customers Pause: The Real Churn Drivers00:08:00 – Facing the Hard Truth: Falling Behind Competitors00:10:30 – The “Hero Model” Approach to GTM Talent00:12:30 – Rebuilding Morale with Comp Structure & Focus00:15:45 – How Enablement Gaps Undermine Performance00:18:20 – Budget Prioritization: Product vs. People00:21:00 – Advice for Vendors Navigating Budget Pushback00:24:15 – Final Thoughts & Partnership Opportunities

    29 phút
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B2B SaaS sales are changing in real-time, and conventional wisdom is becoming quickly obsolete. On the SaaS sales performance podcast, we’ll provide you with the practical tools you need to take advantage of this rapidly changing environment. We read the latest research so you don’t have to. Our masterclasses are distilled down into indispensable practical advice, and we speak to the experts on the front-lines. This is the podcast for anybody wanting to be on the cutting edge of SaaS sales.

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