B2B SaaS Head of Sales

Snapshot

Role: Head of Sales
Company type: VC-backed B2B SaaS selling to mid-market teams
Company size: 30 to 150 employees
Revenue stage: $2M to $15M ARR
Buying authority: Can sponsor budget for sales tooling, enablement, and outsourced support; final approval often with CEO or CFO
Why this segment is interesting: The role owns a hard revenue number and feels immediate pressure when pipeline coverage drops below target.

Pipeline coverage swings week to week because outbound volume is inconsistent across reps.
Forecast calls become defensive because stage definitions are loose and close dates keep slipping.
Reps spend selling time on manual list building, CRM cleanup, and meeting reschedules.
Board pressure focuses on net new ARR, but team quality metrics are lagging or missing.
The Head of Sales feels personally exposed when missed targets are blamed on leadership decisions.

Added a sequencing tool, but adoption dropped after initial onboarding.
Hired one SDR contractor to patch top-of-funnel volume without fixing process quality.
Ran one-off call coaching sessions, but managers did not enforce follow-up standards.
Imported purchased lead lists that produced low reply quality and poor conversion.

Most pipeline problems are execution consistency problems, not market-size problems.
The Head of Sales will respond when the message ties directly to forecast reliability, not generic growth claims.
Urgency is highest within one quarter of a board meeting where target miss risk is visible.
We must validate whether this role can act quickly or is blocked by finance approval cycles.

Your team may have enough leads but no stable weekly outbound execution rhythm.
If close dates slip every forecast cycle, your stage criteria may be too subjective.
Reps doing list operations instead of selling is likely reducing win-rate on active deals.
Most missed quarters start with weak pipeline hygiene six to eight weeks earlier.
If manager coaching is ad hoc, ramp time and message quality usually decay fast.
Outbound volume without account-level targeting often creates meetings that never enter late stage.
Board pressure is easier to handle when forecast confidence is backed by clear qualification rules.

Where in your sales process do deals most often stall, and what usually causes it?
How do you define a real opportunity versus an early-stage conversation in your CRM?
Which part of pipeline creation is hardest for reps to execute consistently every week?
Who must approve budget changes when you need to fix pipeline issues quickly?
What happened the last time you missed a quarter, and what changed after that?
Which metric do you trust least in your forecast review right now?
What internal constraint would block a process change this quarter even if you wanted it?

Positive signal: They describe a current pipeline or forecast problem with numbers and ask follow-up questions.
Positive signal: They volunteer internal context about approval path, team structure, or timeline.
Neutral signal: They acknowledge the problem but defer to a future quarter without concrete trigger.
Neutral signal: They respond politely and ask for materials without sharing specifics.
Strong rejection: They say pipeline is owned by another function and they cannot influence process changes.
Strong rejection: They report no active pressure on pipeline or forecast confidence this year.
Strong rejection: They reject the premise because the problem is currently hiring capacity, not execution quality.
Patterns to log after 100 DMs:

Top three objections by frequency and exact wording.
Reply rate by angle category and first-line framing.
Share of replies from direct decision-makers vs individual contributors.
Most common trigger events: board prep, missed month, rep turnover, or new VP hire.
Average days from first reply to meaningful diagnostic conversation.

Placeholder for validated findings, updated assumptions, rejection clusters, and changes to next outreach cycle.