Know what to ask next.
Sideline is an AI sales coach that sits on your Mac during Zoom, Meet, and Teams calls. The moment the buyer pauses, it gives you the next question. When you hang up, it tells you what you missed, and remembers it for the next call.
Actual overlay, actual size. It sits in the corner of your screen. Nothing joins the meeting.
A recap can’t ask the question for you.
Call recorders tell you on Friday what you should have asked on Tuesday. By then the moment is gone: the budget you skipped, the “we already have something” you treated as a maybe, the next step you left as “let’s stay in touch.”
Parent-company vendor came up. You went straight to the demo.
MissedAsk if this team can buy on its own budget.
→ They have their own budget.
A sixth site opens in October. Nobody asked what that does to timing.
MissedOctober is a real deadline. Lock a date before you hang up.
→ Pilot dated before October.
Spreadsheets and follow-up calls. The cost was never sized.
MissedAsk what those follow-up calls cost them each month.
→ The cost of doing nothing, in their words.
“Send me something.” You said you would, to no one in particular.
MissedBefore you send it, ask who else needs to see it.
→ A name: Priya in ops.
It walks in already briefed.
Teach Sideline once and it carries the context into every call: your playbook, who you’re meeting, and everything that happened with them last time.
Paste your website, or upload the battlecard, pricing sheet, or talk track you’d hand a new hire. Sideline distills your ICP, objections, and discovery framework. You review every change before it’s saved.
Connect Google Calendar or Outlook and the invite tells Sideline which account is on the call. No calendar? Pick the prospect before you start.
Past debriefs for that account come with it: open discovery gaps, unresolved objections, and what you promised.
You’re the seller. Run the call.
A second call with Northwind Health. Last time, “ops” came up and nobody got a name. Pick what you’d say. The coach reacts the way Sideline does: one line, the moment Jordan pauses.
Jordan is on the line. Three moments, two choices each. See what the coach does with them.
Hang up. Get the honest version.
Not a recap of the recording. A coach’s read on how you sold: what you missed, which objections you glossed, a next step with a date on it, and the follow-up email, already written.
Sample debrief. Every field here is something Sideline writes after a real call: the take, missed moments, objections, the live prompt log, commitments with dates, and a follow-up draft that learns from your ratings.
It remembers what you missed.
Every debrief is saved to the account. Next time, Sideline knows what’s still open, coaches you on it live, and checks whether you kept your promises.
The first call leaves gaps.
Budget never came up. “Ops” was mentioned and nobody got a name. You promised an integration one-pager.
The next call picks up the thread.
Sideline loads the last debrief before you join. When the conversation gets close to budget, the prompt knows it went unasked last time.
The debrief closes the loop.
What got resolved, what is still open, and whether you kept your promises, with the line from the call that proves it.
Friendly first call. Discovery is thin: no budget, no timeline, and “ops” never got a name.
“Honestly, the bigger issue is how much time this eats every month.”
Budget never came up last call. Ask what this costs them today.
Jordan: “Thanks for the one-pager, Priya has it.”
One debrief fixes a call. Patterns fix the seller.
Every week, Sideline rolls up your own calls and names the two or three habits costing you deals. Frequent and fixable, each with one concrete change for the next call.
This week
12 calls in view · example reportYou ask about process. You rarely ask what they would pay to replace the current stack.
Fix: after current state, ask “What does this cost you today?” before you demo.
6 pricing objections. 4 handled as “we can look at a smaller package.”
Fix: ask what they compared you to before you move on price.
The coach is already flagging decision process. You are talking through it.
Fix: when the overlay asks who else is involved, ask it that minute.
Private. Your calls, your patterns, nobody else’s dashboard.
A coach for you. Not a bot in the meeting.
Nothing joins the call.
Sideline listens through your Mac’s microphone and system audio. No bot in the participant list. Your buyer sees the same meeting as always.
On your screen, on purpose.
It’s a coach, not a cheat sheet. The point is to make you better at the call, not to hide that you had help.
Yours, not your manager’s.
Your calls, debriefs, and patterns belong to your account. No team leaderboard. No scorecard sent upward.
You’re responsible for telling people a call is recorded where the law requires it. Sideline asks you to confirm your disclosure before your first live call.
Built for people who still sell.
You’re the founder, the closer, and the sales manager. Sideline takes the last job.
Live prompts from your own playbook keep budget, timeline, and decision process from slipping while you sell the vision.
You’re also building the product. Sideline keeps what each prospect said, dodged, and asked for.
Pattern reports show what you keep missing, so your first sales hire inherits the fix, not the habit.
If you want a library of calls to review on Friday, this is the wrong product.
Get coached on your next call.
We’re letting sellers in small waves so each person gets set up properly: playbook loaded, Mac connected, first call coached. Tell us a little about how you sell.