Cracking Outbound

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 teamThe power of consistent training and feedback loopsWhy outbound still works when done rightThings 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 systemHow to coach your team through real-time sales momentsWhy being empathetic but firm is crucial for sales leadershipThings 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 urgencyHow to build trust in long, complex sales cyclesWhy education and community are critical for growthThings 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 changingWhy leveraging first-party data is key to successThe growing importance of smarter cold calling strategiesThings 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

Rob Anderson, CRO at TitanX and former outbound strategist at Docebo and Gong, shares invaluable insights on optimizing sales development. He introduces the Three E Model—Effort, Efficiency, and Effectiveness—for managing SDRs beyond just booking meetings. Rob discusses the evolution of outbound sales strategies, emphasizing the shift to phone-first outreach and the power of client stories. He also explores the role of AI in optimizing BDR capacity and how centralized list-building can enhance sales productivity.

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 painWhy discovery struggles often come back to use casesWhat it takes to build trust as a first enablement hireThings 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

Becca Lindquist, Vice President for the Americas at dbt Labs, tells Todd Busler how she helped grow the company from under $1M to over $100M in ARR, and what it takes to scale outbound without gimmicks.In the episode, Becca digs into what separates good sales leaders from great ones: evolving your seat as the company grows, investing early in enablement, and building outbound muscle across the org, not just in the SDR team.In this episode, you’ll learn:Why top reps generate their own pipelineWhat to look for in your first 50 sales hiresWhat makes pipeline council meetings worth doingThings to listen for: (00:00) Introduction(01:13) How Becca stayed in seat to $100M+ ARR(03:01) Adapting your role as the company scales(06:15) Building outbound systems from day one(07:42) Keeping the PG culture as you grow(09:40) Outbound challenges with open source leads(11:34) Teaching reps to spot real business pain(13:24) Scaling enablement without losing impact(19:29) How dbt runs effective pipeline councils(21:52) Making partner selling actually pay off

Andrew Berger, VP of Revenue at Capchase, shares his journey from cold calling to the nuanced world of outbound sales. He emphasizes the shift from high-volume approaches to focusing on quality and personalization. Lessons from his time at Square reveal the importance of using targeted tools and third-party data for effective outreach. Andrew explains the significance of structuring teams by buyer readiness and the value of rallying around a single clear metric for success. Trust-building with executives and adapting messaging strategies also take center stage.

Creating a winning outbound sales culture starts with the right ingredients.In this episode, Todd Busler, Co-Founder and CEO of Champify, breaks down the six key ingredients for creating a successful outbound sales motion. He talks about the importance of commitment, setting clear expectations, and maintaining a rigorous process.Todd also highlights how focusing on talent, performance management, and continuous testing can accelerate growth.It’s a practical look at the essential elements that drive a thriving outbound sales culture.In this episode, you’ll learn:The six ingredients for establishing a thriving outbound sales cultureWhy a top-down commitment is crucial to successBest practices for skill development and talent managementThings to listen for: (00:00) Introduction(02:26) Six essential ingredients for outbound success(04:34) Establishing a consistent operating cadence for strategy(05:29) Role of revenue operations and support for success(09:23) Motivating the team with rewards and recognition(13:02) Acquiring top talent and effective hiring strategies(15:02) Consistent performance management practices(17:21) No single solution; strong culture is key(18:23) Focus on cold calling and AI preparation

What actually makes an outbound sales engine run at the enterprise level?In this episode, Todd Busler sits down with Zack Sikora, GVP of Sales at Benchling, to talk through what consistent pipeline generation actually looks like at the enterprise level.Zack shares how his time at AppDynamics shaped his thinking around qualification, why AEs must own outbound, and how activity signals can tell you everything you need to know about performance. He also opens up about building a culture where creativity is celebrated, enablement is a priority, and leaders know when to step aside and let reps lead.It’s a front-row look at how structure, storytelling, and small wins can power serious sales results.In this episode, you’ll learn:How to create a PG culture centered on AE prospecting that lastsWhat to track across the sales cycleWhy enablement is your secret advantageThings to listen for: (00:00) Introduction(01:39) Zack’s path through elite sales orgs(02:50) From hardware sales to value selling(05:37) Using activity signals to guide coaching(08:02) Pairing EQ with a process-driven mindset(11:18) Sharing small wins to fuel PG culture(15:03) Leading with outcomes over features(20:19) Why AEs must own their outbound motion(29:37) Enabling sellers with tailored bootcamps(34:33) What outbound could look like with AI