Thirteen Direct Reports and a Prayer [22]

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]

The GUI Is Dead. Long Live the API. [18]

When your buyer asks for an MCP server, can you answer? SaaS vendors are still hiding their API behind the Enterprise tier — and your customers are about to start asking for it. Nate breaks down what API maturity now means for SE leaders, both as buyers and as builders of their own product story. WHAT NATE AND AVA DISCUSS * Why the GUI is becoming the wrong place for products to be evaluated * The backwards pricing logic of "free GUI, Enterprise-only API" * How customer expectations are shifting toward agentic, MCP-aware workflows * The two-way move: audit your own product's API maturity AND your team's vendor selection process THE MOVE This week, walk over to product and ask "what's our API surface, and is it gated behind which tier?" Then add API/MCP availability to your team's own vendor evaluation rubric. Don't pick tools your future workflows can't talk to. ---------------------------------------- 🔗 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]