Surviving Sales Leadership

Most sales leaders treat LinkedIn as a brand exercise. Post a few times a week, get some likes from colleagues, move on. But the reps who are actually self-sourcing pipeline are using it completely differently - they're building their own SQL machine, turning engagement signals into warm conversations before they even pick up the phone.📥 Download the Modern Revenue Leader's Sales Coaching Manual https://bit.ly/3QTbqsJWill Aitken built his entire outbound motion around LinkedIn across three different companies. Niraj Kapur has done 220+ videos and converts inquiries directly from them. Between them and host Tom Boston, there are over 170,000 LinkedIn followers on this episode.In this episode, Will and Niraj sit down with our host Tom Boston to get into what that actually looks like in practice - the content strategy, the video outreach, and the personal vs professional balance that most reps get wrong.In this episode:Why LinkedIn personal brand is an MQL list you build yourself - and take with you when you leaveHow Will uses LinkedIn content to warm up prospects already in his pipeline between stagesNiraj's video outreach approach that generates direct inquiries and how he converts themThe 80/20 rule for personal vs professional content and what happens when you get it wrongWhy the algorithm matters far less than most people thinkHow to use LinkedIn strategically for named accounts, not just broadcasting to the massesThe one question to ask before posting anything: would your CEO share this?About Surviving Sales Leadership:Surviving Sales Leadership sessions help sales leaders tackle their biggest sales challenges in short, focused bursts - we aim to get most episodes done in 30 minutes or less.New episodes fortnight. Subscribe so you don't miss one. 🌐 Episode page: https://www.mysalescoach.com/surviving-sales-leadership-home/how-sales-leaders-build-sql-machine-linkedin🔗 Connect with Tom Boston on LinkedIn 🔗 Connect with Will Aitken on LinkedIn 🔗 Connect with Niraj Kapur on LinkedIn 🔗 Follow MySalesCoach on LinkedInAbout Will Aitken Will Aitken is a sales content creator and coach based in Canada, originally from Milton Keynes. He built his personal brand while working as an account executive and used it to generate his own pipeline - taking that audience with him across three different companies. He's known for honest, direct content about what actually works in sales.About Niraj Kapur Niraj Kapur spent 25 years in sales before founding Everybody Works in Sales, a coaching business working with teams across the UK, Europe and North America. He's done over 220 LinkedIn videos and converts them directly into coaching clients.

Want to be a great coach for your team and drive results in the time you DO have for coaching?Download the Modern Revenue Leader's Sales Coaching Manual---About this episode:Ever had that feeling where your pipeline looks busy… but nothing’s actually moving? Yeah. Turns out, you’re not alone.Sales leaders think stalled deals are a pipeline problem.Sales reps are experiencing something very different.In this episode, Ollie Whitfield sits down with Steve Myers, and John Richardson to unpack insights from analysing 5117 real sales coaching calls and what they reveal about why deals lose momentum.The conversation exposes a gap between what salespeople ask for in coaching and what’s actually holding performance back. While most conversations focus on pipeline, deal progression, and “tips and tricks,” the real blockers often sit deeper—in decision process clarity, mindset, and how sales teams think about control in the deal. The episode explores why decision process dominates coaching conversations, why “closing” is often misunderstood, and how over-reliance on tactics masks underlying behavioural and mindset challenges. It also highlights the disconnect between prospecting responsibility and pipeline ownership, and how this impacts quota attainment and sales velocity.This episode is essential listening for: VPs of Sales, Heads of Sales, Sales Managers and Revenue Leaders who are trying to improve sales coaching effectiveness, increase deal velocity, and build a stronger coaching culture that goes beyond surface-level tactics.Brought to you by MySalesCoach.Learn more about how we support leaders in building elite sales teams with our Sales Coaching Operating System:www.mysalescoach.com

Everything feels like it’s moving—and nothing feels stable.You’re expected to build a high-performing team while the ground keeps shifting beneath you.Want to be a great coach for your team and drive results in the time you DO have for coaching?Download the Modern Revenue Leader's Sales Coaching ManualIn this episode, Tom Boston and Emily Parker break down what it actually looks like to build and lead a sales team inside the chaos of SaaS—where strategy changes, expectations evolve, and pressure never lets up. This episode is for:Sales leaders who are building or scaling teams in fast-moving environments, dealing with inconsistent performance, struggling with hiring decisions, or trying to maintain control and morale while everything around them changes.Inside this sales leadership lesson:Feeling like you’ve “figured it out”… only for messaging, ICP, or strategy to change overnightTrying to lead with confidence when you’re figuring things out in real time yourselfTranslating top-down strategy into something your team actually understands and buys intoHiring people who look great on paper but can’t adapt when the environment shiftsManaging high performers who resist structure and think results excuse behaviourDealing with promotion pressure from reps who think they’re ready—but aren’tKeeping morale high when growth is messy, processes are broken, and support is limitedCarrying extra roles (ops, enablement, HR) while still being accountable for performanceBalancing autonomy with accountability without losing control of the teamBuilding a team that complements each other—not just a group of similar performersAt its core, this episode is about the reality that SaaS growth is rarely clean. Leaders are expected to deliver results while navigating constant change, incomplete systems, and evolving expectations. The ones who succeed aren’t the ones with perfect plans—they’re the ones who can create clarity, build trust, and develop teams that adapt faster than the environment shifts.(00:00) - – Why building a sales team in SaaS still feels chaotic (04:30) - – The real challenge: constant change + managing people through it (08:00) - – Building a balanced team (and why hiring “more of the same” fails) (10:30) - – Leading with clarity when the business keeps shifting (16:00) - – Staying calm and building confidence through uncertainty (21:30) - – Trust, autonomy, and setting boundaries with your team (25:00) - – Hiring realities: coachability, resilience, and what actually matters (33:30) - – Managing promotions, expectations, and team progression pressure (38:00) - – What messy growth really looks like—and how to keep morale high 00:00 – Why building a sales team in SaaS still feels chaotic04:30 – The real challenge: constant change + managing people through it08:00 – Building a balanced team (and why hiring “more of the same” fails)10:30 – Leading with clarity when the business keeps shifting16:00 – Staying calm and building confidence through uncertainty21:30 – Trust, autonomy, and setting boundaries with your team25:00 – Hiring realities: coachability, resilience, and what actually matters33:30 – Managing promotions, expectations, and team progression pressure38:00 – What messy growth really looks like—and how to keep morale highBrought to you by MySalesCoach.Learn more about how we support leaders in building elite and consistent sales teams:www.mysalescoach.com

If deals keep stalling and the story is always “they’ve gone quiet,” the real issue usually showed up much earlier — and it often isn’t being said clearly in coaching.PS.Want to be a great coach for your team and drive results in the time you DO have for coaching?Download the Modern Revenue Leader's Sales Coaching ManualThis session with Steve Myers and Richard Smith gets into the actual reasons deals don’t close, and how deal coaching can surface the truth without turning into a forecast grilling.We break down how to diagnose what’s missing in the deal, validate what’s real vs assumed, and coach reps beyond surface-level reasons into compelling, evidence-backed buying drivers.This is for you if you're a sales leader dealing with:“Close” deals that never close and pipelines full of hope instead of proofReps who can’t clearly articulate why a prospect will actually buyStalled opportunities where next steps were never properly locked inA coaching culture where people tell you what sounds good, not what’s trueIn this episode, you’ll hear the deal-killers hiding in plain sight:Reps mistaking “they want X” for a real problem worth solving“I think…” language replacing evidence — and nobody challenging it properlySurface-level pain (“save time,” “be more efficient”) with no detail behind itDiscovery that never gets to the full three levels of pain: symptom → business impact → how people feel about itNo clear understanding of where budget comes from, how the decision gets made, or where veto power sitsLeaders accepting the rep’s narrative without validating what’s actually happenedWeak upfront contracting — so next steps aren’t agreed, meetings aren’t booked, and deals drift into silenceRepeated stalls that look like a skills issue… but are really discomfort, need for approval, or fear of being too directKeeping a deal alive when the best outcome is clarity to qualify out and redirect effort elsewhereMost deals don’t fail at the end — they fail because the team never got the truth early enough. Great deal coaching creates the environment where the rep can say what’s missing, get specific about the gaps, and leave with clear actions — or the confidence to walk away.Timestamps:0:00 – 5:13 | Creating the conditions for truth: Removing agendas and power dynamics so the real issues surface5:14 – 7:31 | Diagnosing what’s really going on: Buying journey context, decision process clarity, and validating the rep’s story7:32 – 13:02 | The real reasons deals don’t close: Evidence vs belief, solution-language, and coaching to three levels of pain13:03 – 18:10 | Repeat deal failure: Technical vs mindset problems, and why reps don’t use the skills they “know”18:11 – 21:52 | Prep that prevents stalls: Meeting plans, upfront contracting, objectives, and keeping calls on track21:53 – 24:05 | Outcomes that matter: Immediate next actions, strategic skill-building, confidence — and when to qualify outIf you’re a sales leader tired of chasing “almost” deals and want your coaching conversations to surface the truth faster — listen to this episode and start changing how your team diagnoses, not just how they close.PS.Want world class deal coaching for your team? We've got you.Find out more herehttps://www.mysalescoach.com/deal-coachingSurviving Sales Leadership is brought to you by MySalesCoach. Learn more about how we support leaders in building elite and consistent sales teams: www.mysalescoach.com

Sales leaders! Want to build strong teams without burning out in the process?Introducing Surviving Sales Leadership, where each episode is a practical conversation with experienced sales leaders and elite sales coaches about what actually works.Coaching reps, managing pipeline, forecasting, enablement, and navigating growth without everything feeling harder than it should.No “just hold people accountable” nonsense. Real-world tactics and strategies that work in sales right now.If you’re a sales manager, head of sales, sales director, or revenue leader who wants better results, better conversations with your team, and a little more confidence in the chaos, this show’s for you.Subscribe and start surviving sales leadership today!