Best Bits: The Enablement Gap - Why Most New Hires Fail in Their First 90 Days w/ Angel Evenson episode artwork

EPISODE · Nov 16, 2025 · 17 MIN

Best Bits: The Enablement Gap - Why Most New Hires Fail in Their First 90 Days w/ Angel Evenson

from WMYT - What makes YOU Tick? Tech Leaders Career Stories

Founders: You can’t scale if every deal depends on you.But most new hires don’t fail because they’re bad — they fail because you never built the system that sets them up to succeed.Full episode here: https://youtu.be/j4Zr70NsFOk?si=MpffVOPmwDxNs1NgIn this What Makes You Tick: Best Bits episode from the Making Revenue Tick masterclass series, Angel Evenson and Richard Washington break down The Enablement Gap — the silent killer of sales and marketing hires in early-stage startups.If you’ve ever hired someone great on paper who fizzled out fast… this is the 10-minute fix you can’t afford to miss.💡 You’ll Learn:Why experience ≠ impact (and what to look for instead)How founders set up new hires to fail without realizing itWhat real onboarding and enablement should look likeHow to spot multipliers — people who elevate everyone around themWhy structure beats shadowing when you’re scaling salesKey Questions This Best Bits Answers🧩 The Enablement GapWhy do so many talented new hires fail within their first 90 days?What exactly is “enablement,” and how is it different from onboarding?How can founders design onboarding that actually builds confidence and results?💼 Hiring & ExperienceWhy hiring for “years of experience” or big-name logos (like Apple or Meta) is a trap in startups?What kind of experience actually translates well to early-stage environments?How do you spot people who can thrive in fast-changing, ambiguous settings?🚀 Multipliers vs. ExecutorsWhat’s the difference between someone who’s great at their job and someone who multiplies impact across the team?How can you identify “multipliers” in an interview — and what questions reveal them?What signals show a candidate has the confidence and judgment to push back on founders (when it matters)?📋 Onboarding That WorksWhat does a truly effective onboarding program look like — especially for your first GTM hires?How do you transition from “founder in every deal” to a repeatable sales motion without losing quality?Why does shadowing and unstructured “follow me around” onboarding fail?What’s one practical step to document your process and free up founder bandwidth?🧠 Culture & RetentionHow do you build a culture that supports independence, experimentation, and accountability?Why is enabling people before you scale headcount the key to keeping them long-term?👤 About Angel EvensonAngel Evenson is the Founder & CCO of AKA Communications, a sales and marketing consultancy helping founders grow revenue without burning out. A former Challenger consultant, she blends enablement, messaging, and leadership alignment to help early-stage businesses scale sustainably.🔗 Follow Angel: linkedin.com/in/angelevenson📚 Get her tools: linktr.ee/angelevenson🎙️ About the ShowWhat Makes You Tick is hosted by Richard Washington, founder of Tick Talent, featuring conversations with top GTM operators, founders, and executives.Each episode is a masterclass on scaling revenue, building trust, and creating human-centered growth systems.Want help hiring? 👉 Richard Washington – https://www.linkedin.com/in/richwash/🎧 Subscribe to What Makes You Tick for new episodes weekly:YouTube @whatmakesyoutick | Spotify https://open.spotify.com/show/1PrIjRzmSOGUQJSigtpXNS?si=3b350a2f32d84a97 | Apple Podcasts https://podcasts.apple.com/gb/podcast/wmyt-what-makes-you-tick-tech-leaders-career-stories/id1699043715#FounderLedSales #SalesLeadership #StartupGrowth #WhatMakesYouTick #AngelEvenson #WMYT #Enablement #SalesTraining

Founders: You can’t scale if every deal depends on you.But most new hires don’t fail because they’re bad — they fail because you never built the system that sets them up to succeed.Full episode here: https://youtu.be/j4Zr70NsFOk?si=MpffVOPmwDxNs1NgIn this What Makes You Tick: Best Bits episode from the Making Revenue Tick masterclass series, Angel Evenson and Richard Washington break down The Enablement Gap — the silent killer of sales and marketing hires in early-stage startups.If you’ve ever hired someone great on paper who fizzled out fast… this is the 10-minute fix you can’t afford to miss.💡 You’ll Learn:Why experience ≠ impact (and what to look for instead)How founders set up new hires to fail without realizing itWhat real onboarding and enablement should look likeHow to spot multipliers — people who elevate everyone around themWhy structure beats shadowing when you’re scaling salesKey Questions This Best Bits Answers🧩 The Enablement GapWhy do so many talented new hires fail within their first 90 days?What exactly is “enablement,” and how is it different from onboarding?How can founders design onboarding that actually builds confidence and results?💼 Hiring & ExperienceWhy hiring for “years of experience” or big-name logos (like Apple or Meta) is a trap in startups?What kind of experience actually translates well to early-stage environments?How do you spot people who can thrive in fast-changing, ambiguous settings?🚀 Multipliers vs. ExecutorsWhat’s the difference between someone who’s great at their job and someone who multiplies impact across the team?How can you identify “multipliers” in an interview — and what questions reveal them?What signals show a candidate has the confidence and judgment to push back on founders (when it matters)?📋 Onboarding That WorksWhat does a truly effective onboarding program look like — especially for your first GTM hires?How do you transition from “founder in every deal” to a repeatable sales motion without losing quality?Why does shadowing and unstructured “follow me around” onboarding fail?What’s one practical step to document your process and free up founder bandwidth?🧠 Culture & RetentionHow do you build a culture that supports independence, experimentation, and accountability?Why is enabling people before you scale headcount the key to keeping them long-term?👤 About Angel EvensonAngel Evenson is the Founder & CCO of AKA Communications, a sales and marketing consultancy helping founders grow revenue without burning out. A former Challenger consultant, she blends enablement, messaging, and leadership alignment to help early-stage businesses scale sustainably.🔗 Follow Angel: linkedin.com/in/angelevenson📚 Get her tools: linktr.ee/angelevenson🎙️ About the ShowWhat Makes You Tick is hosted by Richard Washington, founder of Tick Talent, featuring conversations with top GTM operators, founders, and executives.Each episode is a masterclass on scaling revenue, building trust, and creating human-centered growth systems.Want help hiring? 👉 Richard Washington – https://www.linkedin.com/in/richwash/🎧 Subscribe to What Makes You Tick for new episodes weekly:YouTube @whatmakesyoutick | Spotify https://open.spotify.com/show/1PrIjRzmSOGUQJSigtpXNS?si=3b350a2f32d84a97 | Apple Podcasts https://podcasts.apple.com/gb/podcast/wmyt-what-makes-you-tick-tech-leaders-career-stories/id1699043715#FounderLedSales #SalesLeadership #StartupGrowth #WhatMakesYouTick #AngelEvenson #WMYT #Enablement #SalesTraining

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Best Bits: The Enablement Gap - Why Most New Hires Fail in Their First 90 Days w/ Angel Evenson

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This episode was published on November 16, 2025.

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Founders: You can’t scale if every deal depends on you.But most new hires don’t fail because they’re bad — they fail because you never built the system that sets them up to succeed.Full episode here:...

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