Director of Outbound Sales (Chicago) Job at The WFS Group, Chicago, IL

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  • The WFS Group
  • Chicago, IL

Job Description

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This range is provided by The WFS Group . Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$70,000.00/yr - $120,000.00/yr

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:

What the heck is a Director of Outbound Sales, anyway? Imagine someone who loves building sales machines from scratch, wakes up thinking about buyer journeys, and has a borderline romantic relationship with pipeline metrics. This role is not about simply managing reps—it’s about architecting the outbound motion from top to bottom.

As our Director of Outbound Sales, you’ll design the overall outbound sales motion including the targeted list building process, messaging frameworks, implementing tech tools, standing up SDR workflows, and launching campaigns that bring in net-new revenue like clockwork. You’ll work closely with leadership (yes, that means the CEO) to shape our go-to-market motion and turn outbound into a predictable, scalable growth channel.

We need someone who’s already done this—who can come in, roll up their sleeves, and bring a proven outbound playbook with them. This is your chance to build the outbound engine of your dreams—no legacy junk, no bureaucratic bottlenecks—just white space and a big goal.

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 (open to other tools, you'll have the freedom to install and deploy your dream tech stack)
  • 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 'emJob Type: Full-time

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 - $120K

Seniority level

  • Seniority level

    Director

Employment type

  • Employment type

    Full-time

Job function

  • Job function

    Sales and Business Development
  • Industries

    Business Consulting and Services

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Job Tags

Full time, For contractors, Remote work, Monday to Friday,

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