Harry Monkhouse runs global outbound at LastPass, 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 and Terminus, 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

Few people have reshaped an outbound culture quite like Jade Campbell.

Now leading mid-market sales at Envoy, 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, 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

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 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

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 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?

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 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

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 plans
• What makes outbound messaging stand out in crowded inboxes
• How to use PLG signals and swarm tactics to generate a pipeline

Things 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

Outdated prospecting playbooks are holding back pipeline growth.

Bridget Conneely, Director of NA Business Development at Recorded Future, joins Todd Busler to walk through how her team transitioned from a broad commercial focus to a fully named account strategy. With experience hiring 400+ BDRs and building global programs at Riverbed and Mimecast, Bridget shares how she coaches young talent into high performers. She discusses redefining success metrics, leveraging LinkedIn as a primary channel, and partnering with marketing for an ABM-first model. 

You’ll also learn about the shift from static product training to story-driven role plays, using small pilots for experimentation, and the importance of personal motivation, AE alignment, and clear scorecards to keep her team focused through change.

In this episode, you’ll learn:

• How Recorded Future moved to a 100 percent named account strategy
• Why LinkedIn now drives the majority of the outbound pipeline
• What behaviors predict success in junior reps early on

Things to listen for: 

(00:00) Introduction

(01:55) Selling a mission that matters

(03:29) Shifting from broad outbound to ABM

(05:07) Mapping ICPs using sales and voice data

(06:55) Leading BDR change without losing momentum

(08:59) How LinkedIn became 80% of the pipeline

(12:23) Coaching young reps into confident sellers

(16:56) Using story-driven enablement to win deals

(20:30) Tying promotion paths to skill-building

(22:26) Experimenting with channel-led SWAT teams

(25:34) Building high-trust BDR and marketing partnerships

(28:54) Traits Bridget looks for in every BDR hire

ChurnZero turned an inbound-heavy team into an outbound machine.

Sarah Kiley, Chief Sales Officer at ChurnZero, joins Todd Busler to share how she transformed a historically inbound-heavy sales team into a consistent outbound pipeline engine. With years of experience in government, nonprofit, and EdTech sales, Sarah brings a unique perspective on operational excellence, team culture, and process-driven growth. 

Sarah shares how she restructured outbound from the ground up, using a process-first approach. She also explains why every rep at ChurnZero now builds their own "sales math" and how personal goals keep their team motivated. 

In this episode, you’ll learn:

• How to transition from inbound to outbound without breaking what works
• The role of sales math and personal goals in performance
• Why outbound fails without clarity in process and ownership

Things to listen for: 

(00:00) Introduction

(01:37) Applying for a role that Sarah had to have

(03:36) Unlocking customer insights without a CSM team

(05:30) The pivot from inbound to outbound

(08:09) Culture and clarity during transformation

(10:10) Building process without killing culture

(12:56) A broken prospecting loop and how to fix it

(14:03) Sales math, quotas, and personal goals

(17:53) Learning from SDR wins and feedback

(23:36) Segmenting reps by market for scale

(27:44) How CS teams drive real pipeline

(32:51) Missteps slowing down B2B sales orgs

Bonus for podcast listeners:

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We’re helping teams like S&P Global generate 20% of their pipeline this way. No complex setup. Just results.

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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 creation
• Why alignment starts with consistent meeting rhythms
• What behaviors top reps show before the deal closes

Things 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 metrics
• What real enablement looks like in practice
• Why coachability matters more than experience in hiring

Things 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