Cracking Outbound

Why Curiosity, Not Cold Calls, Drives Pipeline Today with Harry Monkhouse

Harry Monkhouse [https://www.linkedin.com/in/harrymonkhouse/] runs global outbound at LastPass [https://www.lastpass.com/], where most people still know them as a password manager. But with 35M+ users and a brand-new B2B product, his team is building a pipeline from scratch, without a strong outbound history to lean on. In this episode, Harry breaks down how he’s using trigger-based plays, website signals, and old-school cold calls to drive meetings. We talk about why he left AE life to return to SDR leadership, what he learned from 6sense [https://6sense.com/] and Terminus [https://terminus.com/], and why AI agents will change the game way sooner than most people think. If you care about pipeline, hiring, or where outbound is headed, this one’s worth your time. In this episode, you’ll learn: * Why AI agents might replace parts of the BDR role in 3 years and what to do about it now * How to run outbound with a massive B2C user base and minimal historical motion * Why the best reps and managers focus on trigger-based selling and consistent playbooks Things to listen for:  (00:00) Introduction (01:19) Why outbound leaders should think more like operators (02:32) Lessons from working at 6sense and Terminus (04:58) Trigger-based outbound plays that still work in 2025 (06:38) How stepping back into BDR leadership changed Harry’s career (09:13) The one skill Harry hires across every region (11:40) What AI is already doing well in outbound (13:25) How reps should think about AI agents in the near future (15:32) What selling looks like at a company with 35M B2C users (18:19) Turning personal users into a B2B pipeline (20:06) Using BDRs to drive customer expansion—not just net new (22:28) Coaching reps to work both expansion and outbound motions (24:41) The case for warmth: why outbound doesn’t have to be cold (25:57) Where Harry sees the next big outbound opportunity (27:44) Why most companies promote the wrong people into BDR leadership

How To Create Accountability Without Burning Out Your Sales Team with Jade Campbell

Few people have reshaped an outbound culture quite like Jade Campbell [https://www.linkedin.com/in/jaderyan/]. Now leading mid-market sales at Envoy [https://envoy.com], she’s spent the last six years building the company’s SDR function, shifting the org from inbound-heavy to outbound-driven, and managing one of the highest-output AE teams in SaaS. In this conversation with Todd Busler [https://www.linkedin.com/in/todd-busler/], Jade breaks down the frameworks she uses to create real accountability from pipeline-sourced goals to a live inbound router based on weekly performance. She explains how she motivates Gen Z reps without lowering the bar, how she changed behavior without overwhelming her team, and why most leaders underutilize deal reviews and dashboards. If you manage a team or are trying to drive more outbound motion in a tough market, this one’s worth your time. In this episode, you’ll learn: * How Jade reworked Envoy’s outbound motion without overwhelming her team * Why she built an accountability system tied to pipeline, not just activities * What she does differently to earn rep trust and run a high-output team Things to listen for:  (00:00) Introduction (01:49) Jade’s background and role at Envoy (02:56) Evolving from visitor management to a workplace platform (03:13) Product marketing roots and how it shaped her sales approach (05:27) Fixing early outbound: blast emails and fuzzy ROEs (07:14) Why she shifted the team to a hybrid inbound-outbound model (09:07) Building early systems: where she started and what paid off (11:06) The enablement strategy behind multi-product selling (13:34) What she got right and wrong with outbound messaging (16:52) Meltwater’s intense sales culture and how it shaped her standards (18:53) Managing Gen Z reps with high expectations and real trust (21:29) The mistake new CROs make when they try to “fix” sales orgs (25:48) How she approaches performance management and tough calls (28:31) The weekly pipeline rule that decides who gets inbound (33:13) Building a true outbound culture at a formerly inbound org (36:52) Making sales culture fun without sacrificing performance (39:13) What keeps Jade motivated as a sales leader

What Great Founders Get Wrong About Sales with Liam Mulcahy

Few people have observed as many go-to-market strategies as Liam Mulcahy [https://www.linkedin.com/in/liam-h-mulcahy-32329431/]. The Operating Partner at Kleiner Perkins [https://www.kleinerperkins.com/] 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 job * Why founders’ beliefs about sales can make or break your career * What the next generation of elite sellers will look like Things 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

Finding Green Space in Complex Sales Orgs with Scott Peyser, VP-Ops at CBTS

Outbound success doesn’t come from working harder; it comes from focusing smarter. In this conversation with Todd Busler, https://www.linkedin.com/in/scott-peyser-2088b3/Scott Peyser [https://www.linkedin.com/in/scottpeyser/] 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 [https://www.cbts.com/].  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 logos * Why consistent pipeline inspection drives healthier forecasting and growth * What traits does Scott look for when hiring high-performing outbound reps Things 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?

What It Took to Get 400 New Customers a Month with Terry Falk

Many sales leaders come from quota-carrying roles. Terry Falk [https://www.linkedin.com/in/terence-falk/] started as a corporate lawyer. Now VP of Software Sales at 8am [https://www.8am.com/], 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 communication * What happens when inbound drops and you’re not ready * How to lead teams closing hundreds of SMB deals per month Things 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