Outbound Squad

In this episode, Jason and Todd Caponi from Sales Melon, talk about why AI is just the latest chapter in a story sales has seen many times before. They dig into why more buyer information never replaced the seller, mapping buyer behavior onto your current sales stages, celebrating lost deals to sharpen qualification, and the five core jobs of a first-time CRO.

Check out more free content and get help with outbound at https://outboundsquad.com/.⁠

In this episode, Jason, Joey Gilkey, and Rob Anderson from TitanX, talk about why outbound is moving from the volume era to the precision era. They dig into why fewer reps and more activity rarely hit the number, calculating cost per conversation and per meeting, how parallel dialing drags down connect and conversion rates, and the account dossiers TitanX's reps used at the event.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and Chris Farwell from Octave, talk about how to coach and lead enterprise reps who may already be better sellers than their managers. They dig into finding the problems buyers actually need to fix, translating technical pain into margin and cash flow, knowing when to coach reps and when to just tell them, and turning customer relationships into warm intros.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Scott Leese from Scott Leese Consulting, talk about building a career and income that don't depend on any one job. They dig into why personal brand might be the last career moat, when to start earning outside your W2, his 10-a-day plan for growing your network, and how he builds his calendar around family time.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Ryan Heaphy from Fractal Software, talk about what it takes to build a repeatable sales motion in early-stage vertical SaaS. They dig into why the VP of Sales hire usually flops, what a world-class sales playbook actually includes, reverse-engineering quota from pipeline, and what cold calling looks like in vertical SaaS. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Alex Kremer from Alluviance, talk about why 70% of sales pros are struggling with their mental health, the two wells analogy and the hungry ghost trap, rewiring where your motivation comes from, and selling from presence, not pressure.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Brandon Jackson, formerly of Common Room and now at Ping Identity, talk about his four-pillar CPAD framework for SDR leadership, why dial counts aren't the real measure of a good day, aligning SDR with marketing and sales at once, and where AI belongs in the SDR workflow, and where it doesn't. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jasonand Matt Rogers from Neo4j, talk about breaking into a cold enterprise territory in person, the monthly accountability one-on-one to run with every rep, the hero move that traps first-time leaders, and using AI to scale coaching without watching every call. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Heath Barnett, formerly of Mixmax, talk about why PLG and product-led sales aren't the same thing, the three layers of a real ICP, account scoring with sub-scores that stack, and why AI investment flops without rep skill investment. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and Krysten Conner, sales coach at https://krystenconner.com, talk about the where-we-win report every new AE should run, the ship jumper move and other warm-path openers, ghost-writing a referral email your champion will send, and running EMT discovery on outbound-led calls. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason, Clara Johnson, and Amanda Long from Outbound Squad, talk about why outbound needs its own methodology, the three core parts of Too Good To Ignore, how to scale it across your team, and practical plays your reps can use to book more meetings. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and Amanda Long from Outbound Squad, talk about the daily practice ritual that took her to the top of the leaderboard, how she made it impossible for her manager not to promote her, and how to nail your first front-line leadership role. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and Mark Haas from AdRoll, talk about why the top rep is often the worst first-time manager, his journey from programmer to rep to VP, and how he runs his day-to-day leading revenue.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Alex Murphy from 30 Minutes to President's Club, talk about cold calling without the telemarketer feel, the offering mindset that keeps your self-worth out of the outcome, and his 3-question discovery checklist for first calls.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and John Eitel from Orum, talk about why top sales teams admit they haven't cracked AI, how to centralize AI through RevOps without hurting rep productivity, why skill still beats tool stack, and the pipegen mix by segment that holds up from high velocity to enterprise. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Ashley Kelly from Rippling, talk about how Rippling scaled from 40 to 400 BDRs in under four years, the "go and see" value that runs from Parker on down, and the SDR-to-CRO program that keeps reps around.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and Siobhan Sweeney, formerly of Shopify, talk about her journey from door-to-door sales rep in New York City to first-time sales leader, why she made the jump into enablement, how Shopify built a world-class enablement org, and her take on executive presence, managing up, and coaching reps.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason guests on The Revenue Insiders to talk about Outbound Squad's Too Good To Ignore outbound methodology and its three pillars (disqualify, offer, provoke), the trigger, tension, trust messaging model that works across cold call, email, and social, and what it actually takes to build pipeline in 2026.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com/.⁠

In this episode, Jason and Tito Bohrt from AltiSales, talk about his 4-part framework for building and diagnosing sales orgs, what's working in cold calling right now, and whether the SDR function is about to get replaced. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason and Adam Block from Motive, talk about why they made the move up market, how they protected the mid-market and SMB business that was already working, how they rewired the culture for outbound, and the talent and metrics that matter when you're leading a 3,000-plus revenue org.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠