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Executive Search

Hiring Early to Growth Stage Sales Leaders: 5 Red Herrings That Trip Teams Up

Sara Beth Preston
2 min read

Hunt Club is seeing a surge in clients building Sales teams – from pods of AEs to new leaders who can ramp ahead of Q1 2026. The stakes are clear: hit plan with fewer tools, leaner headcount, and faster time-to-impact.

But hiring Sales leaders is where many teams stumble. Pedigree and past W-2s get overweighted while contextual proof gets ignored. The result: big logos on resumes, weak performance in zero-to-one or mid-scale environments.

Here’s what to watch for as you craft your hiring and interview plan

1. Big logos ≠ Contextual success

What worked under a powerhouse brand often breaks at an emerging company without that brand capital.

What to look out for instead

  • Require proof of wins in your context (deal size, sales cycle, ICP, ACV stage).
  • Ask for 3 specific deals where they created demand without brand tailwinds and score for environment match: brand strength, channel mix, sales motion (inbound vs outbound).

2. "I built the playbook” — Without receipts

Slick slides, no system. Quota may reflect they ran an inherited playbook, not one they built end-to-end.

What to look out for instead

  • Ask for artifacts: enablement docs, stage definitions, dashboards, hiring plans, comp plans.
  • Run a whiteboard: “From 0 → first 10 wins” and have them sequence ICP, channel, messaging, and pipeline math.

3. "I lead from the top"

AKA they’re too far from the grind. If they haven’t personally closed in years, can they sell in a lean setup (no SDR/BDR, scrappy tooling, ambiguous process)?

What to look out for instead

  • Run a live role-play: cold open → discovery → ob jection handling → next step. Inspect calendar screenshots (last 90 days): evaluate customer time vs. internal and calibrate expectations.
  • First 90 days include direct selling targets.

4. Pipeline pretender

Looks strong with perfect inbound; disappears at zero. Can they source, sequence, and multi-thread from scratch, or only work what lands in the queue?

What to look out for instead

  • Ask for their outbound system: list-build, triggers, messaging, weekly volume, conversion rates. Inspect personal pipeline hygiene (notes, follow-ups, next steps).
  • Give a target account list. Have them craft a first-call agenda and followup cadence. 

5. Network Flexor

A big Rolodex ≠ durable revenue. The test is whether they can turn cold or lukewarm contacts into qualified opportunities.

What to look out for instead

  • Separate access from execution: “Show 5 net-new logos where you had no prior relationship.”
  • Score on deal mechanics (multi-threading, mutual close plans, legal and contractual navigation).

Quick takeaway

Big quota = great rep” is a trap. That number can ride a hot product, a lucky territory, or a manager who carried the load. What you want is receipt-based proof – personally sourced pipeline in the last 12–18 months, repeatable outbound mechanics, and deals won without brand tailwinds.

Hire the operator who can create demand, not just collect it.

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