Director of Sales

Director of Sales

Continuum · Chicago (West Loop) · Hybrid (2 days/week onsite)

Reports to: VP of Sales

Leads: 4 Commercial Account Executives + 4 Business Development Representatives

Required: If you’re interested in this role, please complete the Culture Index assessment here:

About Continuum

Continuum is disrupting an untapped, winner-take-all, $22B+ market of B2B reverse logistics. We are the first and only network-deployed platform that solves complex multi-party returns, warranties, and repairs across supply chains. Our mission: if a product moves up the supply chain in B2B distribution or manufacturing, we own it.

The role

We’re hiring a Director of Sales to lead Continuum’s commercial engine: a team of Commercial AEs and BDRs that generate and close revenue at high intensity.

You’ll own the number and the plan to hit it. Because of the systems and tooling we’ve built, your team spends 80%+ of their time on revenue-generating activity: selling and sourcing, not administrative drag.

You’re stepping into an advanced playbook and a modern, AI-enabled sales system that are already in place. Your job is to run them at a high level and win, not rebuild them. This is a hands-on, lead-from-the-front seat: you’ll be in the deals, coaching live and personally influencing outcomes, while raising the whole team’s execution. You’ll work closely with the VP of Sales, the Head of GTM Engineering, and Revenue Operations, a level of systems, data, and leverage most sales leaders never get.

What you’ll own

· The commercial revenue number: pipeline, conversion, and closed-won across your team.

· The deals. Lead from the front: join key calls, shape deal strategy, and personally influence outcomes across the commercial book.

· Live coaching. Work deals shoulder-to-shoulder with your reps: model great discovery, multi-threading, and negotiation, and lift the team’s execution against the playbook.

· Team productivity and funnel performance. Keep the team operating at the top of its range, with high-intensity selling and sourcing, disciplined targeting and cadence, and rising conversion. The systems handle everything that isn’t revenue-generating.

· Forecast integrity. Hold the line on qualification discipline and deliver a forecast leadership can plan against, free of happy-ears optimism.

· A tight loop with GTM Engineering and Revenue Operations. Turn the systems, data, and tooling they build into closed revenue, and feed the field’s signal back to sharpen them.

· Hiring A-players, consistently. Run our structured, evidence-based hiring process, scored objectively against a defined profile.

Requirements and skills

Track record

· Team leadership. You’ve led B2B sales teams, ideally both a closing team and a BDR/SDR function, and consistently hit or beaten team targets.

· Leads from the front. You’re a strong closer who personally moves deals, not a manager who only inspects them.

· Sector experience (bonus). You’ve sold supply-chain or ERP-adjacent software into manufacturers and distributors.

How you think and lead

· Systems thinker. Sharp analytical horsepower. You see the whole revenue machine, how sourcing, conversion, and tooling interact, and optimize the system, not just the rep.

· Data-driven. You lead from the numbers, find the insight, and turn it into a coaching or process decision, fluent alongside Revenue Operations and GTM Engineering.

· Force multiplier. You take an already-advanced, AI-enabled system and get everything out of it, running it hard and raising the ceiling on what already works.

· Challenger. Teach, tailor, take control.

· Forecaster. You hold qualification discipline and run a clean, multi-stage funnel.

Who you are

· Intellectually honest. Direct and coachable, you’d rather be challenged than validated.

· Grit. Perseverance and a bias for action.

· Develops people. You develop others and lift the whole team’s execution.

Why join Continuum?

· You’ll work alongside experienced operators. This is a team of people who have built and scaled before. You’ll be sharpened by peers who challenge you, not the only operator in the room.

· A genuine moat, at a moment that rewards one. As SaaS businesses everywhere struggle to differentiate, and face a real threat of becoming irrelevant, Continuum has built a durable competitive moat: a network-deployed platform no single manufacturer, distributor, or point tool can replicate.