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Director of Sales Development
Director of Sales DevelopmentThe WFS Group • Chicago, IL, US
Director of Sales Development

Director of Sales Development

The WFS Group • Chicago, IL, US
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Job Description

Job Description

A Snapshot of WFS Group :

WFS Group is a high-performance sales agency that delivers “done-for-you” sales solutions for growth-stage companies. Our clients outsource their sales function to us—from individual SDRs and closers to full teams—and we build the systems, processes, and talent to drive real revenue.

We’ve made our mark in the online education and coaching space, and we’re now expanding into SaaS and B2B markets—bringing our outbound expertise and tech-enabled sales ops to new verticals. Whether it’s inbound, outbound, or full-cycle—we build sales engines that scale.

Position Overview :

We’re looking for a builder. Someone who doesn’t just manage sales teams but architects end to end outbound systems that drive predictable, scalable growth. You wake up thinking about buyer journeys, pipeline velocity, and how to make every outreach touch smarter, not louder. You’re equal parts strategist and operator obsessed with process, performance, and people.

As our Director of Sales Development, you’ll own the entire outbound engine from top to bottom : refining ICPs, designing messaging frameworks, implementing tech tools, standing up SDR workflows, and launching campaigns that generate new revenue on repeat. You’ll work closely with leadership (yes, including the CEO) to shape our GTM motion, scale the team, and make outbound a true growth discipline not just a numbers game.

We’re looking for someone who’s already done this. Someone who can build a world-class SDR department and cold outreach engine from scratch, roll up their sleeves when needed, and bring a proven outbound playbook to life. This is your opportunity to build the outbound engine of your dreams. No legacy systems limitations, no bureaucracy, just a blank canvas and a clear mandate : build something exceptional to lead our entire outbound SDR service.

You SHOULD apply to this role if :

You’ve built an outbound B2B sales motion from scratch before and can’t wait to do it again

You have a unique multi layered list building process that incorporates intent and leads to the highest response rates

You love mapping buyer journeys and creating repeatable, multi-touch outreach strategies

You have had success building omni channel multi touch campaigns that leverage both automation and human SDRs

You have a sixth sense for messaging that lands, and you aren’t afraid to test bold ideas

You’ve managed SDRs / BDRs and know how to coach them to quota

You get excited about tools like Apollo, Clay, HubSpot, and Outreach.io

You’re passionate about pipeline visibility, CRM flows, and data-driven decisions

You’ve got a system for everything—from list building to lead routing to lead scoring

You love being both a strategic advisor and a tactical operator

You’ve seen firsthand how outbound, when done right, can be a rocket fuel for growth

You thrive in a fast-paced, high-autonomy, “build-as-we-go” environment

You SHOULD NOT apply to this role if :

You’ve only ever managed inbound sales teams

You need a fully built system handed to you

You’re intimidated by building outreach frameworks, tech stacks, and SDR teams

You think cold outreach is “dead” 🙄

You aren’t comfortable reporting directly to senior leadership or being held accountable to revenue outcomes

You don’t enjoy experimentation, iteration, or rapid change

You have an overall understanding based on concept & theory but wouldn’t know the actual steps to take to get it done from end to end

You struggle to communicate clearly across departments (sales, ops, marketing, etc.)

You’re allergic to CRM tools, KPIs, and dashboards

You’re not excited by the idea of building something world-class from the ground up

Major Roles & Responsibilities :

Architect and lead our outbound B2B sales strategy—owning everything from ICP refinement and messaging to tech stack & cutting edge tools

Build scalable outbound playbooks and cadences across email, phone, LinkedIn, and more

Integrate AI-powered tools for outreach personalization, automation, and lead scoring

Stand up and manage SDR / BDR workflows—set quotas, talk tracks, and coaching rhythms

Select and optimize our outbound tech stack (Apollo, Instantly, Clay, Salesloft, Outreach, HubSpot, etc.)

Develop and manage list-building, lead sourcing, and segmentation strategies

Create performance dashboards, activity benchmarks, and outbound KPIs

Continuously test outreach variables to improve reply rates and conversion

Partner with Sales Ops and Marketing to ensure outbound aligns with company-wide GTM strategy

Build processes that scale—laying the foundation for a repeatable, high-performing outbound engine

Coach with clarity, lead with data, and drive results with zero fluff

Required Experience :

2+ years minimum owning outbound sales strategy in a B2B environment (In SaaS specifically is a huge plus)

Deep experience with enterprise sales cycles and high-ticket service offerings

Track record of building outbound sales processes, tech stacks, and SDR teams

Familiarity with the full outbound toolkit : Apollo, Clay, Instantly, HubSpot, Salesloft, etc.

Strong operational chops—you think in systems, not just scripts

Ability to work cross-functionally with Sales Ops, RevOps, and Marketing

You’ve built dashboards and know your way around CRM logic, lead routing, and lifecycle stages

Bonus if you’ve worked in the agency, coaching, or alternative education space

Huge bonus if you’ve got the receipts—case studies, success metrics, and a few war stories to go with 'em

Pay : $70,000.00 - $120,000.00 per year

Compensation package :

Bonus opportunities

Commission pay

Uncapped commission

Schedule : Monday to Friday

Work Location : Remote

Compensation Range : $70K - $185K

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Director Of Development • Chicago, IL, US

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