Highly Adaptive

In this episode of Highly Adaptive, Jeff Pelliccio and Erin MacKenzie are joined by Mark Winter of WinSource Group to deliver a reset sales leaders need heading into 2026: clarity comes before decisions. Because when a year has been rough, leaders tend to reach for the same three levers—new markets, new tech, new hires—without first getting brutally honest about where the business actually is.

Mark breaks the “survival kit” down with real operator math: start with retention, understand what revenue you’re truly at risk of losing, and work backward into what it will actually take to grow. He also makes a bold case for the most important lever in modern sales execution: the middle manager. If your sales managers can coach, reinforce, and create guardrails, you can outperform teams with bigger “rockstar” reps but no leadership system.

The conversation closes with a definition that reframes consultative selling for staffing and professional services: it’s not asking one extra question—it’s proving impact in the customer’s metrics, not your own. And the banner takeaway lands clean: you’re not entitled to much at work, but you are entitled to clarity—because without it, nobody behind you can win.

Key Takeaways

• Clarity before decisions – Don’t choose a path until you can accurately name where you are right now.

• Retention math comes first – Start with what you’ll keep, then calculate what you must replace and grow.

• Middle managers are the multiplier – Strong sales leadership beats great reps with no coaching layer.

• Be careful with “magic” investments – Tech and data tools can be great—at the wrong time, they’re expensive distractions.

• Consultative selling = customer metrics – You’re consultative when you can measure your impact in their world, not yours.

• Do the work (in the field) – Presence, conversations, and consistent effort still produce returns—fast.

Sponsors

Allied Insight - The Preferred Marketing Partner of Staffing and Consulting Businesses
Build a go-to-market strategy that matches reality. Allied Insight helps staffing and consulting leaders clarify positioning, align teams, and execute marketing that supports revenue—not noise.

All Things Staffing - Expert Resources for the Staffing Community
Your hub for staffing insights, operator frameworks, and practical resources. All Things Staffing helps leaders turn sales and leadership lessons into actions that improve performance.

In this season one retrospective episode of Highly Adaptive, Jeff Pelliccio and Erin MacKenzie go behind the scenes on what they learned from launching the show—fourteen episodes, seven guests, and a surprising number of moments that turned into repeatable leadership frameworks. It’s part highlight reel, part synthesis, and part preview of what’s coming next.

They revisit the analogies that helped complex ideas land (from change bridges to “candy cane traps”), the leadership lessons that stuck, and the simplest “Monday actions” listeners can actually take—like tightening account penetration through org charts, strengthening onboarding touchpoints, and using curiosity as a competitive advantage.

The episode closes with a forward-looking reset: the industry isn’t just reacting to change—it’s leading it. And season two kicks off with a strong run of topics designed to help staffing and professional services leaders make clearer decisions and move faster with confidence.

Key Takeaways

• Synthesis beats noise – A season’s worth of episodes reveals the patterns leaders can actually use.

• One completed initiative wins – One finished priority beats five half-done ones every time.

• “Monday actions” matter – The best insights turn into simple next steps (org charts, follow-ups, onboarding checks).

• Curiosity is a strategy – Give teams time to test, play, and learn—then operationalize the wins.

• Your community is the advantage – The best ideas spread when leaders share what’s working (and what isn’t).

• Momentum into 2026 – The season two preview keeps the thread: practical frameworks, real operators, no fluff.

Sponsors

Allied Insight - The Preferred Marketing Partner of Staffing and Consulting Businesses
Transform your firm’s go-to-market readiness the way you transform your marketing. Allied Insight helps staffing and consulting leaders clarify their message, align teams, and execute strategies that drive real results.

All Things Staffing - Expert Resources for the Staffing Community
Your hub for industry insights, practical frameworks, and real-world guidance. All Things Staffing helps leaders turn big ideas—AI, sales, culture, and operations—into action.

In this episode of Highly Adaptive, Jeff Pelliccio and Erin MacKenzie get practical about something most leaders treat as seasonal—but the best companies treat as strategic: recognition. They unpack why gratitude isn’t a random thank-you note, a pizza party, or a gift basket on autopilot. It’s a deliberate, repeatable leadership behavior that drives engagement, improves retention, and strengthens culture in a way your competitors can’t easily copy.

The conversation breaks down what a real culture of gratitude looks like: tying recognition to values, making appreciation specific (the why matters), and building simple systems that make recognition visible without turning it into a checkbox. They also explore the nuance leaders often miss—how to scale recognition without losing authenticity, and why “systems” only work when they preserve the human element.

If you want culture to be more than a poster on the wall, this episode gives you a clear starting point: begin small, make it consistent, and lead from the top—because gratitude might be the fastest path to culture transformation you’ll find.

Key Takeaways

• Specific beats generic – Recognition lands when it’s tied to a real moment and a clear “why.”

• Tie gratitude to values – Culture shifts faster when appreciation reinforces the behaviors you want repeated.

• Make it visible – Public recognition builds community and reinforces standards across teams.

• Top-down starts it – Leaders set the tone; consistency from leadership creates momentum everywhere else.

• Systems help—human touch wins – Tools can amplify recognition, but they can’t replace authenticity.

• Start small, scale intentionally – Build a phased approach you can sustain, then expand.

Sponsors

Allied Insight - The Preferred Marketing Partner of Staffing and Consulting Businesses
Build a culture and brand people want to be part of. Allied Insight helps staffing and consulting leaders align message, leadership, and execution—so your internal culture matches the story you tell the market.

All Things Staffing - Expert Resources for the Staffing Community
Your hub for frameworks, insights, and operator-grade guidance. All Things Staffing helps leaders turn culture initiatives and leadership ideas into practical actions that stick.

How many staffing leaders are actually satisfied with their tech stack—not just tolerating it, but genuinely getting what they were promised? In this episode of Highly Adaptive, Jeff Pelliccio and Erin MacKenzie welcome Leanne Courtney of Achieve With Tech to diagnose why that demo excitement so often turns to regret within six months.

Leanne brings a refreshingly direct perspective shaped by years helping organizations untangle duplicative tools and misaligned expectations. The conversation opens with an unexpected detour through Australian wildlife facts (including why 97% of koalas have chlamydia and the tragic origin of Leanne's Segway fears), before diving into the real problem: most organizations let vendors tell their story instead of building their own first.

The trio unpacks why ROI has become a meaningless buzzword without baseline metrics, how one client discovered they had four different tools doing the same thing, and why "change management" should really be called "user enablement management." Leanne introduces her Stop, Adapt, Adopt framework—a practical methodology for breaking the cycle of tech disappointment that treats technology decisions like building Tetris blocks rather than eating an entire cake.

Whether you're drowning in analysis paralysis or wondering why your team won't use the expensive software you just implemented, this episode provides the mirror-holding questions and concrete steps to make your next technology decision stick.

Key Takeaways

• Build Your Story Before the Demo — Define your complete workflow and success metrics before letting vendors tell you what you need; organizations that wait for someone else to tell their story end up with tech that doesn't match their internal processes
• ROI Means Nothing Without Your Definition — Software companies can't tell you what success looks like for your business; establish your baseline metrics first, then partner with vendors to measure against your specific outcomes
• Stop, Adapt, Adopt Framework — Pause to analyze what problems you actually have, adapt your expectations and processes to reality, then adopt technology that fits your current state rather than an idealized future
• User Enablement Over Change Management — Don't force technology down people's throats; identify naturally curious team members as evangelists and seek to understand their daily reality before expecting adoption
• Start Small, Build Tetris Blocks — Resist the urge to solve everything at once; pick one process, one problem, one building block and stack incrementally rather than buying the whole cake
• Ask About Roadmaps Both Ways — When evaluating vendors or consultants, ask what specific outcomes they'll achieve in six months; authentic partners will also ask about yours to ensure alignment

Sponsors

Allied Insight — The Preferred Marketing Partner of Staffing and Consulting Businesses Before your next tech investment, make sure your story is clear. Allied Insight helps staffing leaders build the strategic foundation that makes technology decisions stick—because the best demo in the world can't fix misaligned expectations.

All Things Staffing — Expert Resources for the Staffing Community Your hub for frameworks that cut through the noise. All Things Staffing delivers the practical insights that help leaders stop reacting and start building technology strategies with intention.

In this refreshingly honest episode of Highly Adaptive, Jeff Pelliccio and Erin MacKenzie strip away the polish and get real about their AI journeys. Opening with Jeff's admission that his AI tools might know him better than his wife (and Erin's confession that she could ask AI for her own gift recommendations), this episode becomes part confession, part cautionary tale, part practical guide for anyone drowning in the AI deep end.

The hosts bare all, from Jeff's embarrassing second prompt ever ("taco recipes" immediately after asking about 2023 marketing priorities) to Erin's one-sentence discovery prompts and eventual breakup with Claude (they've since reconciled). Through their candid sharing, they reveal how quickly the learning curve can steepen—one contact went from zero to expert in just 45 days, inspiring Jeff's own AI marathon that had him burning through paid credits building reporting tools.

From personal wins like Jeff's Japanese interpreter for communicating with in-laws to professional breakthroughs like Erin's case study agents that interview clients directly, the conversation showcases both the silly and the strategic. They share their "operational plumber" moments where AI exposed data gaps, their favorite LLMs for different tasks, and hard-learned lessons about keeping agents simple enough not to consume their own outputs.

Whether you're still at the taco recipe stage or building complex predictive analytics, this episode provides the roadmap for harnessing AI without losing your mind—or your humanity.

Key Takeaways

Start with Problems, Not Tools – Don't adopt AI because everyone else is; identify what's slowing your team down first

Practice Makes Prompts – Treat prompts like job descriptions: role, responsibility, rules, background, output expectations

Agents Need Training Too – The more context, examples, and feedback you provide, the smarter your AI becomes

Stay Simple or Suffer – Complex agents can consume their own outputs; start basic and build incrementally

Different LLMs for Different Jobs – ChatGPT for deep reasoning, Claude for writing/coding, Perplexity as the workhorse

AI Redesign > AI Automation – Ask "If we built recruiting from scratch with AI, what would humans vs. machines handle?"

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Sponsors

Allied Insight - The Preferred Marketing Partner of Staffing and Consulting Businesses
Navigate your AI journey with marketing partners who understand both technology and humanity. Allied Insight helps staffing leaders build strategies that leverage AI without losing their authentic voice.

All Things Staffing - Expert Resources for the Staffing Community
Your hub for practical AI insights and real-world applications. All Things Staffing delivers the frameworks that help leaders harness AI for competitive advantage, not just novelty.