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Director of Sales

Insight Global
Boca Raton, FL Full Time
POSTED ON 4/25/2026
AVAILABLE BEFORE 5/24/2026

Overview

We are hiring a Sales Director to build and lead a new Growth Team focused on expanding our managed and recurring revenue business. This leader will own the strategy and execution for pipeline generation, deal pursuit, and account expansion across managed services and subscription/recurring offerings. You will partner closely with Marketing, and establish a repeatable sales motion, and deliver predictable ARR/MRR growth.

Key Responsibilities

  • Build and lead a high-performing Growth Team (hiring, onboarding, coaching, performance management) focused on managed services and recurring revenue.
  • Own and deliver quarterly and annual new ARR/MRR and expansion targets; establish forecasting rigor and pipeline hygiene.
  • Define the go-to-market strategy, segmentation, and ideal customer profile (ICP) for managed/recurring offerings; translate strategy into measurable plays.
  • Create a repeatable sales motion, including discovery, qualification, value messaging, pricing/packaging alignment, and proposal/SoW standards for managed services.
  • Drive pipeline generation in partnership with Marketing (campaigns, outbound sequences, events, partner initiatives) and ensure efficient lead-to-opportunity conversion.
  • Lead complex deal cycles from first meeting through negotiation and close; structure multi-year agreements and renewals to optimize retention and growth.
  • Implement and improve sales operating cadence: weekly pipeline reviews, account planning, QBRs, deal desk/approval flows, and CRM data quality.
  • Represent the Growth Team in cross-functional planning; ensure alignment of capacity, delivery readiness, and customer success outcomes.

Required Qualifications

  • 8 years of B2B sales experience with at least 3 years leading a sales team.
  • Proven track record of meeting/exceeding revenue targets, including recurring revenue (ARR/MRR), renewals, and/or account expansion.
  • Experience selling managed services and/or subscription-based offerings with multi-stakeholder, consultative sales cycles.
  • Demonstrated ability to build new sales motions (plays, messaging, process) and scale them with a team.
  • Strong forecasting, pipeline management, and CRM discipline (e.g., Salesforce, HubSpot, Dynamics, or similar).
  • Excellent communication and executive presence; able to translate customer problems into outcomes and business value.
  • Comfort operating in ambiguity and a builder mindset—able to create structure, iterate quickly, and drive change.

Preferred Qualifications

  • Background in recurring revenue GTM (packaging, pricing, renewal/expansion playbooks, churn mitigation).
  • Experience building outbound prospecting programs and partnering closely with SDR/BDR functions.
  • Familiarity with services delivery and operating models (SLA, SOW, utilization/capacity planning) and their impact on sales commitments.
  • Experience selling through partners or building alliance/channel motions.
  • Bachelor’s degree or equivalent practical experience; MBA a plus.

Salary : $120,000 - $150,000

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