Your New Head of Sales Just Started. Now What?
Early alignment and trust-building are key to unlocking their impact in the first 90 days.
Quick note before we jump in: Huge congrats to Stage 2 Co-Founder and Managing Partner, Mark Roberge on the upcoming release of The Science of Scaling! đ This book breaks down the exact frameworks that complement the questions we tackle each week on Dear Stage 2. If youâre working through how to grow go-to-market the right way, this belongs on your desk. Pre-orders are available nowâand 100% of the proceeds go to mental health.
DEAR STAGE 2: We just brought on our first Head of Sales and want to set them up for success. What can we do as a founding team to help them hit the ground running? ~READY TO RAMP
DEAR READY TO RAMP: Bringing on a Head of Sales is a pivotal moment. Youâve likely been running founder-led sales up to this point, or maybe have hired 1-2 AEs to join you on the founder-led journey, but now youâre âhanding over the reinsâ to someone with deep sales experience. But hereâs the thing: even the best sales leader canât perform in a vacuum.
I spoke with Terry Lee, a Stage 2 LP, CRO at Arkitechture and seasoned go-to-market operator. His advice centers around creating clarity, building trust, and ensuring alignment between the new sales leader and the rest of the organization.
Hereâs how to set your Head of Sales up to thrive:
Clarify What Good Looks Like
Your Head of Sales needs a clear mandate. What are they being hired to do? Build the team, grow the top of funnel, mature the sales process, or just hit this yearâs revenue target? Terry advised:
âAligning around goals and priorities is very important at this stage. A new Head of Sales is often eager to start building a team and scalable processes, but someone needs to transition the pipeline from the founders, ensure that the pipeline is accurate, current, and properly documented, and that deals are closing or you are in trouble from day one. Then, once you are closing deals or helping to deliver on that first forecast, you can worry more about additional processes, tools, new hires, etc. There is no better first board meeting than communicating that the forecast is being achieved. â
Get on the same page early about:
Your expectations for the next 30/60/90 days.
The state of the current pipeline, team, and forecast.
What success looks like in the next 12â18 months.
This is especially critical if youâre moving from founder-led sales to a formal sales function. Your new hire needs to know where the handoff starts and ends.
2. Get Them into Deals Immediately
Your new sales leader doesnât need a two-week onboarding course. They need to get in front of customers and prospects, hear how your customers talk about your product, see how your sales team runs a call, etcâŚ
Encourage shadowing and participation in current deals for at least the first 30â45 days. This helps them absorb:
How youâve positioned the product.
Where buyers get stuck.
Whatâs been working (and maybe more importantly, what hasnât).
âDonât fall into the trap of âneeding to understand the business or understand the marketâ before you jump into sales calls. Start participating in sales calls immediately. Customers donât expect you to know that much and your goal should be to just listen anyway. Also participate in Customer Success calls, what do happy customers sound like, go to events. You need to hear what the market is saying directly as quickly as possible.â
Early exposure will help them quickly spot patterns, build credibility with the team, and start shaping the playbook for whatâs next.
Share Your âSales Mathâ
A successful sales leader canât operate without context. Share your current funnel math, including conversion rates, average deal size, sales cycles, and win/loss data. If you donât have all of this buttoned up yet, give them what you can and then make it a joint effort to define and track it together.
Whatâs your historical lead-to-close conversion rate?
What kind of pipeline coverage do you expect?
How have reps historically hit quota (if anyone has)?
Terry recommends every new sales leader leans in here. If you understand the historical performance and the goals of the business, you can start working (quickly) to improve performance:
âOnce you understand the goal you can set a corresponding KPI. Is it bookings or ARR, is it NDR or GDR, new leads or conversion, etc? And then you need to understand whether the data in your CRM is worth anything. Most likely you need to clean that up and improve your sales process so that whatever KPIs you choose are being accurately monitored and reported going forward.â
This baseline becomes the foundation for forecast accuracy and performance reviews.
Let Them Lead (but Donât Disappear)
You hired this person to lead sales, so let them. But donât vanish.
Be available. Provide air cover and remove blockers. Help them build cross-functional trust with marketing, product, and customer success. And coach them on how decisions get made at your company.
The most effective founders donât just delegate a function. Instead they stay close, ask smart questions, and give feedback frequently in the first 90 days. Terry advises:
âIt is incredibly important to make sure the CEO, the CFO and the CRO spend a lot of time aligning, getting to know each other and creating a cadence for reporting and checking in. Too often, everyone breathes a sigh of relief when the CRO comes on board and expects them to take it from there.â
Align the Board Early
Your Head of Sales will likely join the next board meeting. Donât let that be the first interaction. Set up intro calls with key board members early on and brief your new hire on:
What the board cares about (beyond just âhitting the numberâ).
Any landmines to avoid in presenting or forecasting.
What questions theyâre likely to get asked.
A confident, informed first impression goes a long way in earning board trust and buying time if things get bumpy.
A successful sales leader is a multiplier, but only if you set them up with the right tools, trust, and time to lead. We hope this helps as you bring on your newest executive team member.
Until next year!
Thatâs right, weâre taking next week off - enjoy the last few days of 2025 and weâll see you in 2026!