Cracking Outbound

Few people have observed as many go-to-market strategies as Liam Mulcahy.The Operating Partner at Kleiner Perkins has led sales at MongoDB, helped founders at Unusual Ventures find product-market fit, and has a front-row seat to what separates breakout companies from the rest.In this conversation with Todd Busler, he shares how top sellers should evaluate startups before joining, what founders often overlook when building their first sales team, and why making fast decisions beats perfect ones in early-stage growth. He also explains why technical fluency is quickly becoming the edge for modern sellers and what the best GTM teams all do to stay ahead in 2025.In this episode, you’ll learn:How to vet an early-stage company before taking the jobWhy founders’ beliefs about sales can make or break your careerWhat the next generation of elite sellers will look likeThings to listen for: (00:00) Introduction(02:21) Liam’s background and role at Kleiner Perkins(03:27) How to pick the right company to join(05:59) Evaluating founders’ views on sales(08:24) Why signed contracts are the new competitive moat(10:31) The changing definition of “early-stage” in the AI era(12:22) What real market pull looks like(15:13) How to tell if a founder believes in sales(24:27) What top early-stage GTM teams do differently(27:16) Decision velocity over decision perfection(33:21) Challenger selling vs. Value selling(39:44) The rise of technical sellers and the 2030 prediction

Outbound success doesn’t come from working harder; it comes from focusing smarter.In this conversation with Todd Busler, Scott Peyser discusses how they built systems that keep their operations running smoothly, from pipeline inspection frameworks to compensation levers to disciplined outbound cadences. After leading large teams at Dell, helping UiPath scale through its IPO, and shaping revenue operations at Clari, he’s now VP of Operations at CBTS. Scott shares what he’s learned building and refining outbound motions at every scale, from hypergrowth SaaS to billion-dollar service firms. He explains how clarity, consistency, and culture drive performance. Teams win when they inspect the pipeline with intention and commit real time to prospecting. The discipline is evident in the fundamentals, such as carving out time for outbound efforts, conducting weekly pipeline reviews, and focusing energy on areas with the most significant growth potential.In this episode, you’ll learn:How UiPath shifted its outbound motion to focus on expansion over new logosWhy consistent pipeline inspection drives healthier forecasting and growthWhat traits does Scott look for when hiring high-performing outbound repsThings to listen for: (00:00) Introduction(01:40) Lessons from UiPath’s hypergrowth and IPO experience(03:18) Building strong process discipline at EMC and Dell(04:12) The three pillars of effective outbound motion(05:41) Using compensation levers to drive net new pipeline(06:56) Forecasting pipeline and early pipeline metrics(08:00) CBTS’s shift to a services-first strategy(09:40) Creating repeatable revenue from expansion(13:23) Building trust and culture through guiding principles(15:51) Leading through tough quarters without losing the team(20:27) Hiring for intellect and drive in go-to-market roles(27:20) Why fast no is better than long maybes(29:23) Can SaaS reps sell services?

Many sales leaders come from quota-carrying roles. Terry Falk started as a corporate lawyer.Now VP of Software Sales at 8am, he oversees a team closing 400 new customers every month. He shares with Todd Busler how legal training shaped his approach to sales and why his time managing complex contracts helped him think clearly under pressure. He also breaks down the mistakes that slowed his early sales leadership, how he learned to build a pipeline without relying on inbound, and what running a high-velocity SMB motion looks like today.Listen in for a refreshingly honest take on getting better by going through the fire.In this episode, you’ll learn:How legal experience can sharpen sales communicationWhat happens when inbound drops and you’re not readyHow to lead teams closing hundreds of SMB deals per monthThings to listen for: (00:00) Introduction(01:36) What legal training taught him about enterprise sales(04:49) Early sales leadership mistakes at a Series A startup(08:31) How he structured a repeatable outbound pipeline(13:46) Balancing selling and hiring in early-stage roles(15:51) What changed when inbound suddenly dropped(17:24) High-velocity SMB sales explained through a “closing call”(19:59) Shark Tank-style outbound and why it wasn’t scalable(26:18) Finding their ICP using win data, not personas(29:40) Why outbound in SMB SaaS looks very different(34:28) Reps chasing whales vs. reps targeting coral reefs(40:34) Using AI for seller ops instead of seller strategy

Most outbound messaging gets ignored, Reps miss their quota, and the pipeline suffers. Why is this happening?Meredith Chandler, Head of Sales at Aligned, joins Todd Busler to analyze and discuss what it takes to build outbound that actually performs. With experience at Samsara, Spiff, and pclub.io, she shares how her team uses PLG signals to drive pipeline, why reps should build their own 90-day plans, and how coaching shifts from scripts to scorecards.Join us in this episode as she shares all her tips to help sales reps’ outbound messaging reach their goals.In this episode, you’ll learn:How to coach reps to build and own their own 90-day plansWhat makes outbound messaging stand out in crowded inboxesHow to use PLG signals and swarm tactics to generate a pipelineThings to listen for: (00:00) Introduction(01:49) Why selling sales tech is different(03:20) Building outbound from scratch at multiple startups(06:14) How she hit 76% open and 16% booking rates(07:23) Using swarm tactics and memes to drive engagement(09:02) Turning PLG signals into coordinated outbound(10:57) Prioritizing leads with intent scoring(12:07) Aligning BDRs, marketing, and RevOps for plays that convert(15:36) How she creates a high-performance culture(17:11) Coaching reps to think beyond the CRM(18:41) Onboarding reps to 150% quota in their first quarter(20:02) The biggest mistake in most onboarding plans(24:58) Why reps must own their 90-day plan(26:38) Peer coaching and personalized growth paths(28:04) How business acumen drives performance(29:30) Why she coaches outside her day job(31:47) Misconceptions about digital sales rooms(33:43) Selling in a new category without getting outsold

Bridget Conneely, the Director of NA Business Development at Recorded Future, shares her extensive experience in hiring over 400 BDRs. She details how switching to a named account strategy transformed their sales performance. The conversation dives into the vital role LinkedIn plays in driving their outbound pipeline and how Bridget coaches young sales talent through story-driven training. She also emphasizes the importance of aligning AE teams and motivation to keep momentum during change. Experimentation and strong leadership are key themes, making for an insightful discussion.

Discover how ChurnZero transformed from an inbound-heavy sales team to an outbound powerhouse. Sarah Kiley shares her insights on creating a process-driven team culture that maintains motivation through personal goals. Learn about the crucial role of 'sales math' in achieving performance clarity and how to successfully navigate the shift from inbound to outbound without losing momentum. Get tips on fixing prospecting issues and the importance of collaboration between sales and marketing to drive growth. This transformation offers valuable lessons for any sales organization.

Discipline and ownership are the fuel that drives winning sales teams.Toby Carrington, Chief Business Officer at Seismic, joins Todd Busler to share how leading operations, marketing, and SDRs under one roof has shaped his view of modern pipeline generation. With experience scaling global teams and advising early-stage startups, Toby brings a system-level lens to go-to-market execution. He talks about focusing on the structures, feedback loops, and alignment needed to make success repeatable and resilient, regardless of market shifts or company stage.He explains why the best sales orgs prioritize discipline, cadence, and cross-functional alignment, and how personal pipeline ownership has become a leading indicator of rep success. Drawing from Seismic’s enterprise growth journey, he breaks down how platform selling changes rep behavior, coaching, and capacity planning.In this episode, you’ll learn:How Seismic operationalizes rep-led pipeline creationWhy alignment starts with consistent meeting rhythmsWhat behaviors top reps show before the deal closesThings to listen for: (00:00) Introduction(02:51) Unifying ops, marketing, and SDRs for growth(06:42) Feedback loops between product and GTM(08:34) Enablement's rise to the C-suite(13:31) Why rep-led pipeline wins more often(15:01) Cadence and accountability that drive results(21:55) The hidden cost of bad-fit deals(22:19) Selling to all rooms of the house(31:08) PG Tuesdays and focused pipeline bursts(35:44) Cutting AI sprawl with in-flow tools(39:33) Using 1mind to increase inbound conversion

When you’ve been coached by the best, you carry that torch forward.David Boyle, founding partner at RevCentric Partners, shares how a passion for enablement and a history of working alongside sales legends led him to build a consulting firm focused on revenue performance. He reflects on the foundational lessons from PTC and BMC, and why those experiences shaped his approach to pipeline creation and talent development.In this episode, David breaks down the three failure points most CROs face and how to fix them with process, messaging, and consistent live coaching. He explains why sales messaging must be persona-specific, what real adoption looks like, and how great leaders hire and retain top talent by teaching the craft.In this episode, you’ll learn:How to measure pipeline strength with stage two metricsWhat real enablement looks like in practiceWhy coachability matters more than experience in hiringThings to listen for: (00:00) Introduction (02:04) Why sales legends stay in the trenches(04:56) Core habits learned at PTC and BMC(06:49) Three major breakdowns CROs face in pipeline(08:01) How to increase qualified meetings without hiring(09:22) Why most sales messaging never actually works(13:35) Why sales trainings fail without live coaching(17:29) What sellers really want from enablement teams(18:34) How great leaders turn playbooks into performance(22:11) The three must-have traits for every great seller(24:09) Non-negotiable traits every sales hire must have(28:11) Boyle’s response to skeptics of classic sales frameworks

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 motionWhat great rebound messaging actually looks likeWhy sales reps must become product expertsThings 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 ratesHow to make every sales stage buyer-facingWhat reps should stop waiting on marketing to doThings 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