Thirteen Direct Reports and a Prayer [22]

Two Pillars, One Team [23]

Why product enablement and sales enablement should never share a calendar. An SE leader running thirty SEs across multiple markets split his enablement into two completely separate tracks: an internal team for product knowledge and an external partner for sales skills. They never overlap — and that's the point. WHAT NATE AND AVA DISCUSS * Why a single enablement team always defaults to product training when a release ships * The blind-spot problem when the people who teach the product also coach positioning * Why continuous external coaching beats two-day workshops — the half-life is days, not months THE MOVE Split your enablement into two tracks. Internal team owns product knowledge, demos, technical onboarding. External partner owns sales methodology, discovery, positioning. Protect both calendars equally — the moment a product release eats your sales skills time, you're back to one pillar pretending to be two. ---------------------------------------- 🔗 Resources & Links: paths.to/presales [https://paths.to/presales] 📅 Book a Discovery Call: calendly.com/serockstars-tim/discovery-call [https://calendly.com/serockstars-tim/discovery-call]

Thirteen Direct Reports and a Prayer [22]

Why the time to build a team-lead layer is before you need one. An SE leader scaled from three to thirteen direct reports in eighteen months before getting team leads approved. By the time he got the structure, he wasn't coaching anyone — he was doing triage. WHAT NATE AND AVA DISCUSS * The hidden cost of "I can still manage them all" — strategic work, enablement programs, hiring ahead of demand * Why you should start building the team-lead case at six to eight direct reports, not thirteen * How to spot your informal leaders before the formal role exists — and avoid the classic mistake of promoting your top performer into a job they'll hate THE MOVE If you have more than six direct reports and your team is still growing, start the team-lead conversation with your leadership today. Build the case around what you could be doing with freed-up capacity — and start identifying the SEs other SEs already go to for advice. Don't wait until you're drowning to ask for a lifeboat. ---------------------------------------- 🔗 Resources & Links: paths.to/presales [https://paths.to/presales] 📅 Book a Discovery Call: calendly.com/serockstars-tim/discovery-call [https://calendly.com/serockstars-tim/discovery-call]

Hire for Domain, Train for Sales [21]

Why a controller in your customer's office may onboard faster than a senior SE. An SE leader scaling from five to twenty SEs stopped hiring from the presales talent pool. His last six hires were former controllers and accountants from his customers' world — and they got into customer meetings independently in three months instead of four. WHAT NATE AND AVA DISCUSS * Why domain credibility in a vertical product can't be faked or taught quickly * The 80/20 enablement flip — minimal product training, heavy investment in sales skills and roleplay * The retention edge: domain hires aren't comparing your SE role to another SE role at a competitor THE MOVE If you're in a vertical product company struggling to find SE talent, look at your customer's org chart. Rewrite the job description around the domain ("deep understanding of financial close processes") instead of years of presales experience — then redirect the budget you save on product training into structured sales skills development. ---------------------------------------- 🔗 Resources & Links: paths.to/presales [https://paths.to/presales] 📅 Book a Discovery Call: calendly.com/serockstars-tim/discovery-call [https://calendly.com/serockstars-tim/discovery-call]

Liability Is the Moat [20]

When demos commoditize, accountability wins the deal. When demos commoditize and AI-first competitors look better on paper, what wins deals? Nate makes the case that accountability is now the durable moat — and explains how SE leaders need to retrain teams to sell it. WHAT NATE AND AVA DISCUSS * Why auditors, lawyers, and tax advisors still get paid in an LLM world * The CFO question that ends most AI-first vendor pitches: "if the model is wrong, who pays?" * Why accountability can't be demoed — but it can be told * Where to find the stories that aren't in your sales library yet THE MOVE This week, pull your team's last ten customer reference stories. Read each one with a single question — "is this about features delivered, or outcomes owned?" The ratio tells you exactly where to invest in training and content this quarter. ---------------------------------------- 🔗 Resources & Links: paths.to/presales [https://paths.to/presales] 📅 Book a Discovery Call: calendly.com/serockstars-tim/discovery-call [https://calendly.com/serockstars-tim/discovery-call]

Show Me Your Release Cycles, Not Your Roadmap [19]

Roadmaps are wishlists. Release notes are receipts. Roadmaps are wishlists. Release notes are receipts. Ava walks through how she now evaluates every vendor when she's buying software for her own team — and why the way she buys today is exactly how her customers will buy from her tomorrow. WHAT NATE AND AVA DISCUSS * Why a 12-month roadmap is the wrong artifact to evaluate a vendor on * Cadence relative to peer set: how to compare release velocity without comparing to AI labs * The pivot: if SE leaders are doing this as buyers, customers will start doing it too * Why a static one-pager contradicts the velocity message — and how a live release page fixes it THE MOVE This week, pull your product's last six months of public release notes. Build a live page — a URL that compiles from your release feed and updates every time you ship. Put it in front of every SE on your team. ---------------------------------------- 🔗 Resources & Links: paths.to/presales [https://paths.to/presales] 📅 Book a Discovery Call: calendly.com/serockstars-tim/discovery-call [https://calendly.com/serockstars-tim/discovery-call]