Cracking Outbound

Brian Hamor, CEO of BuyerExperience, shares how a missing answer in a board meeting sparked the idea for his company. He recounts his transition from pro basketball to startup operator and how he uncovered a major gap in how teams handle closed-lost opportunities.

In this episode, Brian outlines why win-loss insights alone aren't enough and how revenue teams can turn lost deals into a repeatable growth motion. He explains the rebound funnel, what most teams get wrong after deals fall through, and how AI can be used to re-engage buyers with precision.

In this episode, you’ll learn:

• How to operationalize a closed-lost motion
• What great rebound messaging actually looks like
• Why sales reps must become product experts

Things to listen for: 

(00:00) Introduction 

(01:44) From pro basketball to building GTM systems

(03:04) The startup moment that sparked BuyerExperience

(06:13) Who should lead win-loss: product marketing or sales?

(08:33) Why insights aren’t enough without revenue impact

(10:15) How top teams build systems to win back deals

(12:06) Surprising feedback trends from closed-lost interviews

(14:58) Modeling revenue upside from re-engagement programs

(19:09) Turning buyer feedback into high-converting follow-up

(26:14) Building value cases from AE input before outreach

(28:06) When deeper outbound research is worth the effort

(30:45) What’s next for BuyerExperience’s product roadmap

Rick Kickert, co-founder and CEO of revlogic, joins Todd Busler to share how his time managing million-dollar budgets shaped a radically different approach to sales. Now advising some of the fastest-growing SaaS companies, Rick brings a buyer-first lens to pipeline generation, sales enablement, and revenue process design.

In the episode, Rick shares why chasing massive pipeline numbers often leads teams in the wrong direction, and what top reps do differently to cut through a noisy market. He reflects on a hard-earned lesson from a lost deal that changed how he thinks about differentiation, not as something you sell, but as something you show up with.

In this episode, you’ll learn:

• Why forecasting problems often start with win rates
• How to make every sales stage buyer-facing
• What reps should stop waiting on marketing to do

Things to listen for: 

(00:00) Introduction

(02:50) Why most enablement teams get ignored

(03:46) Metrics that actually move revenue forward

(06:54) What buyers really want from reps

(10:31) How and Why AppDynamics hired a buyer to sell

(13:59) Impostor syndrome and finding your value

(18:16) Mapping sales stages to buyer jobs

(24:29) Standing out in crowded markets

(30:34) Easy ways to differentiate as a rep

(33:08) The painful lesson Rick never forgot

Kyle Asay, VP of Global Growth Sales at LaunchDarkly, shares how he revamped the company’s outbound motion during his first few quarters. He outlines the territory planning shifts, structural changes, and leadership plays that helped drive a 142% increase in pipeline and cut the time to first sale nearly in half.

In this episode, Kyle describes how account segmentation set the foundation, what it took to get long-time reps to buy in, and why simple frameworks have helped his team outperform expectations. He also reflects on managing pressure, avoiding whiplash changes, and what it takes to build trust as a new leader.

In this episode, you’ll learn:

• How to transition from inbound to outbound at scale
• The core three metrics Kyle uses to manage performance
• Why territory planning is the key to faster ramp times

Things to listen for: 

(00:00) Introduction

(03:20) Increasing pipeline 142% with outbound segmentation

(05:00) Territory planning mistakes and how to fix them

(07:50) Getting rep buy-in without causing cultural whiplash

(13:12) Leadership lessons from tough feedback and early missteps

(16:44) The three outcome metrics Kyle never stops measuring

(20:21) Reducing time to first sale through better account focus

(23:23) Tracking rep activity without micromanaging

(26:52) Turning a feature-led product into a platform story

(34:58) Advice on choosing the right sales org and opportunity

(36:33) Mastering internal locus of control in your sales career

(42:06) Staying grounded as a sales leader in high-pressure roles

More pipeline doesn’t always mean more revenue.

Austin Hitchcock, Senior Director of Account Development at Highspot, joins Todd Busler to reveal how he transformed a global ADR organization from product-market fit to a revenue-driving outbound engine. 

Austin shares the hard truth: more pipeline doesn’t always mean better pipeline. He discusses why conversion rates dropped as the team scaled, the impact of adjusting comp plans to reward qualified opportunities over meetings, and how aligning AE-SDR teams boosted performance on both sides.

In this episode, you’ll learn:

• Why SDR comp plans might be hurting your win rates
• How to fix AE relationships without adding more headcount
• What a modern outbound motion actually looks like in 2025

Things to listen for: 

(00:00) Introduction

(01:48) Staying motivated through every company stage

(03:51) Scaling SDRs fast and what broke

(06:27) Why fewer reps improved outbound results

(11:23) Pipeline quality doubled after redefining success metrics

(14:48) What top ADRs do after booking meetings

(17:10) Why pipeline obsession leads to bad decisions

(22:14) How to spot and fix funnel conversion gaps

(31:56) How internships fuel long-term sales talent

(39:31) Career advice for SDR leaders feeling stuck

Isaiah Crossman, former CRO at Tropic, shares his unique journey from account executive to sales leader, discussing how he led his team through explosive growth. He reflects on the importance of finding the right product-market fit and how his approach to outbound sales evolved from his time at Wunderkind to Tropic.

In this episode, Isaiah explains the key role outbound played in his success, the importance of refining sales messaging, and how consistent training and feedback shaped his team’s results. He also dives into the realities of balancing high-volume prospecting with personalized outreach.

In this episode, you’ll learn:

• How to build a high-performing outbound sales team
• The power of consistent training and feedback loops
• Why outbound still works when done right

Things to listen for: 

(00:00) Introduction 

(03:06) Isaiah’s background and journey to Tropic

(06:12) Joining Tropic as the first sales rep

(07:34) The importance of outbound in building the pipeline

(14:54) Why outbound is still effective in today’s sales environment

(18:38) What differentiates top performers from the rest

(25:56) Why generic outbound messaging fails and how to fix it

(27:37) Swapping jargon for clarity in sales messaging
(29:37) Rethinking disqualification: when pushing leads unlocks hidden value
(32:38) A simple two-question framework for effective discovery
(40:23) Planting differentiators early to beat your top competitor
(43:48) Outpacing larger rivals through service and sales execution

Ryan Heinig, Chief Revenue Officer at 2X, shares his journey from leading top B2B SaaS companies like Qlik and AppDynamics to shaping outbound strategies at a growing tech-enabled services firm. He reveals how he successfully scaled outbound efforts by focusing on repeatable systems, strong leadership, and a balance of empathy and accountability.

In this episode, Ryan discusses how shifting from SaaS to services changed his approach to sales, why sales reps must master discovery and qualification, and how to create a culture of high expectations while fostering autonomy.

In this episode, you’ll learn:

• The secret to building a sustainable outbound system
• How to coach your team through real-time sales moments
• Why being empathetic but firm is crucial for sales leadership

Things to listen for: 

(00:00) Introduction

(02:14) Evaluating the opportunity at 2X

(04:46) Selling tech-enabled services vs SaaS

(06:39) Hiring for curiosity and coachability

(08:38) Balancing high expectations with empathy

(14:03) Scaling outbound from AE to CRO

(17:19) Maintaining PG culture across sales segments

(19:25) Leading indicators for outbound success

(23:29) Using AI to enhance research and outreach

(28:27) Overcoming consistency challenges in outbound

(35:31) Defining sales stages that align with buyer’s journey

(40:04) Playing the long game in sales

Understanding your buyer changes everything.

In this episode, Todd Busler sits down with Em Daigle, Founder & Chief Automation Officer at OTTO-MATES, to talk about what it really takes to sell to accounting and finance professionals.

Em shares how her background in public accounting shaped her approach to go-to-market strategy, and why trusted relationships are the key to closing deals in this space. She unpacks what most sales teams get wrong about this audience, how to build long-term credibility, and the value of staying close to your customer.

You’ll also hear how product knowledge, curiosity, and patience can transform how teams connect with technical buyers.

In this episode, you’ll learn:

• Why understanding the buyer matters more than urgency
• How to build trust in long, complex sales cycles
• Why education and community are critical for growth

Things to listen for: 

(00:00) Introduction

(01:32) Selling to accountants starts with trust

(04:06) Why automation needs a human lens

(07:31) Learning from messaging that flopped

(11:06) Aligning product and sales to win

(15:01) Creative events that actually work

(20:24) How accountants really want to buy

(25:08) Curiosity as a sales superpower

(30:36) Adjusting sales motion for new tech

(34:00) Building trust through peer-led learning

Outbound sales strategies are evolving faster than ever with AI. The best teams are starting to look inward at their existing data.

In this episode, Todd Busler, Co-Founder and CEO of Champify, explores the shifts in outbound sales, particularly the move from traditional email tactics to more personalized approaches. He discusses how cold calling is making a comeback, but with smarter, data-driven strategies behind it. 

Todd also shares insights on the role of centralizing outbound efforts and why volume-driven plays just aren’t cutting it anymore.

It’s a thought-provoking discussion on what’s working in 2025 and beyond, and how companies can adapt their outbound strategy for better results.

In this episode, you’ll learn:

• How the outbound sales landscape is changing
• Why leveraging first-party data is key to success
• The growing importance of smarter cold calling strategies

Things to listen for: 

(00:00) Introduction

(02:06) The shift from email to cold calls

(04:17) Centralized AI-first outbound model explained

(05:59) Why automation is losing effectiveness

(07:03) Leveraging first-party data for outreach

(09:02) Re-engaging closed lost opportunities

(11:10) Using closed data for re-engagement

(13:52) Why first-party data gives an edge

(16:53) The future of personalized outbound outreach

Building a successful sales team goes beyond just numbers.

Rob Anderson has built outbound programs at some of the most respected names in SaaS, from scaling Docebo’s SDR engine pre-IPO to shaping enterprise pipeline strategy at Gong. In this episode, he breaks down the systems-level thinking behind it all.

At the center of Rob’s approach is his Three E Model: Effort, Efficiency, and Effectiveness. It’s a framework every sales leader can use to pull the right levers, whether you're trying to get more from your reps, improve conversion across the funnel, or adopt tools that map to outcomes.

If your outbound motion needs structure, control, and clarity, start here.

In this episode, we cover how Rob:

• Operationalized segmentation before AEs caught up
• Turned SDRs into embedded deal contributors, not just meeting bookers
• Built systems that scale without bloating headcount

Things to listen for: 

(00:00) Introduction

(03:17) Scaling outbound at Docebo

(05:05) The importance of phone-first outreach

(09:01) Evolving SDR function from small to global

(11:14) The power of client stories in sales

(15:22) Unlocking insights with technographic data

(17:34) Optimizing BDR capacity with AI

(20:24) Reworking email strategy for awareness

(24:13) Aligning SDR and AE functions

(30:12) Shifting role of outbound sales development

(33:05) Centralized list-building for SDRs

(35:45) Tech tools for modern sales development

How to lead enablement by fixing what’s actually slowing your team down.

In this episode, Todd Busler talks with John Ley, Sr. Director of GTM Strategy & Operations at Brex, about what it really means to make enablement a strategic lever from day one.

John shares how his time at Square and Brex shaped his thinking, why you need more than playbooks and role plays, and what happens when you build tight feedback loops with sales reps. He gets into how real throughput wins often come from collaborating with teams like finance and risk, not just product marketing or RevOps.

You’ll also hear how a practical onboarding framework, strong conviction in your ICP, and a move away from static training decks can unlock meaningful results.

In this episode, you’ll learn:

• How to structure enablement around actual rep pain
• Why discovery struggles often come back to use cases
• What it takes to build trust as a first enablement hire

Things to listen for: 

(00:00) Introduction

(01:44) John Ley’s first priority in enablement at Brex

(04:26) Building a reliable foundation for sales data

(06:06) Removing friction across ops, finance, and risk

(07:33) Rethinking ICP ownership and common traps

(10:21) The Brex approach to early outbound plays

(13:10) A smarter four-part onboarding for new reps

(18:32) Modernizing competitive training with AI tools

(22:04) Advice for CROs hiring first enablement lead