Sales team leader (Head of sales) Job at IspeedToLead, Boston, NY

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  • IspeedToLead
  • Boston, NY

Job Description

What You’ll Own

  • ICP & Segmentation: Define the narrowest winning niches (by GEO, line of business, agency size, buying triggers)

  • Pipeline Creation: Build predictable Seeds / Nets / Spears motion (customer referrals, content/partners, targeted outbound).

  • Playbooks & Cadence: Scripts, objection library, email/LI/phone sequences, discovery frameworks, qualification (e.g., MEDDPICC/BANT).

  • Funnel Instrumentation: Stage definitions, entry/exit criteria, conversion math, 3–4× pipeline coverage, forecast hygiene.

  • Coaching System: Weekly 1:1s, call reviews (≥2 per rep/week), role-plays, scorecards, and performance plans where needed.

  • Revenue Integrity: No sandbagging, no wish-casting—forecast accuracy ±10%.

  • Cross-Functional: Tight loops with Growth/Marketing, Supply, and Ops to align lead quality, routing, and SLAs.

  • Compliance: Sales behaviors aligned with TCPA/DNC and consent workflows.

     

What You’ll Do (Day-to-day)

  • Run a crisp operating rhythm: Daily standups → Weekly pipeline review → Monthly QBR.

  • Manage a small, sharp team (SDRs/BDRs → AEs); specialize roles where it increases throughput.

  • Enforce CRM truth: 100% activity logging, next steps, close dates, probabilities, and exit criteria per stage.

  • Partner with Marketing on lead SLAs, MQL→SQL definitions, and feedback loops to improve targeting and creative.

  • Build the sales content stack: talk tracks, one-pagers, ROI math, case studies.

  • Report leading indicators (inputs) and lagging outcomes (revenue) with driver trees.

     

Success Metrics (your scoreboard)

  • Pipeline creation / rep / week: target set (e.g., $X qualified pipeline).

  • Stage conversion rates: MQL→SQL, SQL→SAO, SAO→Win (each with baselines and targets).

  • Meeting-set rate & Show rate; Discovery-to-Proposal %, Win rate, Sales cycle (days).

  • Forecast accuracy: within ±10% monthly; pipeline coverage 3–4× next-month quota.

  • Rep productivity: quota attainment %, ramp time, time-to-first-deal.

  • Process health: CRM hygiene ≥95%, follow-up SLA p90 < 24h.

30/60/90-Day Outcomes

30 days

  • Audit funnel & data; publish ICP v1 and stage definitions with exit criteria.

  • Stand up base cadences (phone/email/LI) and discovery framework.

  • Install dashboards (activity → meetings → pipeline → revenue) and coaching rhythm.

60 days

  • Hit ≥80% adherence to cadences and CRM hygiene.

  • Pipeline coverage ≥2.5× next-month quota; forecast accuracy ±15%.

  • Objection library v1; 2 repeatable talk tracks with proof of impact.

90 days

  • Pipeline coverage ≥3×; forecast accuracy ±10%.

  • Lift SQL→Win by +20% vs. baseline and reduce cycle time by −15%.

  • Two new “spear” campaigns (high-intent niches) generating ≥30% of new pipeline.

     

Must-Haves

  • 4–7+ years in high-velocity inside sales (preferably lead-gen, adtech, proptech, or adjacent).

  • Team leadership experience: hiring, ramping, coaching, and performance management.

  • Ruthless with numbers: pipeline math, driver trees, forecasting, A/B tests, and quota design.

  • System builder: turns messy inputs into playbooks, cadences, and dashboards.

  • Tools fluency: CRM (SFDC/HubSpot), sequence tools (Outreach/Salesloft), call recording (Gong/Grain), LI Sales Nav, basic BI.

  • English C1. US-friendly hours.

     

Nice-to-Haves

  • Experience selling to agencies/brokers (insurance, performance marketing).

  • Built specialized teams (SDR vs AE vs AM/CSM) and comp plans tied to inputs + outcomes.

  • Familiarity with TCPA/DNC basics and consent/QA workflows.

     

What We Offer

  • Remote-first, high-autonomy, and very high speed.

  • Competitive base + performance bonus

  • A strong AI team (4 Prompt Engineers + Chief of AI) to automate prospecting, research, and follow-ups.

  • We’re okay with smart mistakes—we care about learning speed.

  • After 1 month, we fund any courses/trainings/coaching you want.

Job Tags

Full time, Remote work,

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