Keep selling until you can explain how deals close
Most first sales teams inherit whatever process the founder used to win the early customers. If that process lives only in the founder’s head, a new salesperson starts from nothing and learns by trial and error, with your pipeline as the test.
Before you hire, make sure you can explain why customers buy. Can you describe the companies that said yes, the people who signed, and the problem that made them act? If every deal looks different, keep selling a little longer. A pattern is the most valuable thing you can hand to your first hire.
Write down how deals actually happen
Turn the pattern into a short playbook. It doesn’t need to be polished; it needs to be specific enough that someone new could follow it and tell you where it breaks.
- Ideal customer: the type of company, its size, and the signals that suggest it’s a good time to reach out.
- Buyer: the role that feels the problem and the role that signs.
- Opening: the reasons to reach out that have led to real conversations.
- Objections: what prospects push back on, and the answers that have worked.
- Stages: the steps from first conversation to signed contract, and how long each usually takes.
- Disqualifiers: the conditions that mean a deal is unlikely to close.
Hire for the stage you’re in
Your first salesperson will work with less structure than any rep you hire later. Look for someone who can sell without a complete playbook, ask good questions, and tell you what they’re learning from the market. Experience selling to a similar buyer often matters more than a famous logo on a résumé.
Consider hiring two salespeople instead of one when you can. With a single rep, it’s hard to tell whether a slow quarter reflects the person, the market, or the process. Two people working the same playbook make that easier to see.
Be cautious about hiring a VP of Sales first. A senior leader who expects an established team and a proven process may struggle when the job is still to find one. At this stage, you need someone who will do the selling, not just manage it.
Give new salespeople a real ramp
Even experienced salespeople need time to learn your product, your market, and your buyers. Plan the first weeks deliberately instead of handing over a list of accounts and hoping for the best.
- Have them sit in on sales calls before running their own.
- Give them the playbook, the best recent deals, and the deals you lost.
- Set them up on the tools your team uses, with shared records of prospects and conversations.
- Start with a focused set of accounts that match your ideal customer.
- Agree on early milestones, such as conversations started and meetings held, before expecting closed revenue.
Watch the numbers that move first
Closed revenue takes time to show up, especially with longer sales cycles. In the meantime, track the measures that lead to it, and review them weekly with the team.
- A weekly review in three questions
- What moved forward this week, and why? What stalled, and what will we try next? What did we learn from prospects that should change the playbook?
- New conversations started with prospects who fit your ideal customer.
- Meetings held, not just meetings booked.
- Pipeline created, by stage.
- Win rate and the reasons deals are won or lost.
- Time from first conversation to signed contract.
Get sales leadership before you can hire a VP
A young sales team still needs leadership: someone to refine the playbook, coach the salespeople, and step into the important deals. You don’t have to fill that role with a full-time executive. Advisors, fractional sales leaders, and growth partners who sell alongside your team can all help.
Whichever route you choose, look for three things. The person should be able to close deals, not only advise on them. They should build a process your team keeps using after they step back. And your contacts, conversations, and pipeline should stay in your systems, not theirs.
This is the work Wisp Growth was built for. Our sales leaders build your pipeline, close deals, and get your team selling on Wisp, with the long-term goal of handing over a sales engine your team runs on its own.