Field Sales Representative (Chicago)

About SweatPals

SweatPals is redefining how fitness communities connect and thrive. As a rapidly growing platform bridging fitness enthusiasts with community leaders, we provide comprehensive tools for discovery, management, and monetization. Our mission is to make fitness more social, accessible, and rewarding for everyone involved. SweatPals is proudly backed by some of the best venture capital firms in the world, including Andreessen Horowitz.

Role Overview

As a Field Sales Representative at SweatPals, you'll play a critical role in our Chicago market launch strategy. This pivotal position will help establish SweatPals' presence in one of America's most energetic fitness markets by engaging directly with fitness community leaders at their events. You'll be the face of SweatPals in Chicago, building authentic relationships within the local fitness ecosystem and driving our expansion in the Midwest.

This role uniquely combines relationship building with strategic business development, serving as the foundation of our Chicago growth strategy through genuine community engagement.

What You'll Learn and Achieve

Market Launch Excellence

• Gain unparalleled experience launching a tech platform in one of America's most dynamic fitness markets

• Develop expertise in market entry strategy and execution

• Build a comprehensive understanding of Chicago's unique fitness landscape and community dynamics

• Create and implement strategic plans for penetrating specific Chicago submarkets (Downtown, North Side, South Side, West Loop, etc.)

• Master the art of building brand presence from the ground up in a competitive market

• Contribute directly to executive-level strategic planning for Midwest expansion

Community Building & Network Development

• Cultivate an extensive network within Chicago's influential fitness community

• Develop deep relationships with fitness thought leaders across diverse neighborhoods and activity types

• Gain expertise in authentic community engagement and relationship-based selling

• Master the art of translating social capital into business opportunities

• Build valuable content creation skills for social media and community marketing

• Become a recognized connector within Chicago's fitness ecosystem

Sales Strategy & Business Development

• Transform relationship-building skills into measurable business results

• Develop expert qualification and needs assessment techniques

• Master consultative discovery processes that identify operational challenges and growth opportunities

• Build analytical skills by evaluating community leaders' technology stacks and business processes

• Create compelling business cases that demonstrate clear value propositions

• Develop skills in timing and closing demo opportunities with high conversion rates

Territory Mastery & Strategic Planning

• Become an authority on Chicago fitness communities and emerging trends

• Build expertise in pipeline management and strategic territory planning

• Develop data-driven decision-making skills for maximizing impact across a diverse market

• Create effective coverage strategies across community types and geographic areas

• Learn to identify and track meaningful market activities and outcomes

• Spot emerging fitness trends with potential business implications

Collaborative Sales Ecosystem

• Develop crucial skills in cross-functional collaboration with Partnership Managers

• Master the art of preparing comprehensive prospect briefs that drive successful demos

• Build expertise in setting up colleagues for success through effective handoffs

• Develop a feedback mindset that contributes to continuous improvement

• Learn to balance independent field work with team collaboration

• Build skills in supporting the full sales cycle from first contact to close

Qualifications

Required

• Passion for fitness and community building

• Strong knowledge of Chicago geography and fitness landscape

• Strong interpersonal skills with ability to connect authentically

• Self-motivated with excellent time management abilities

• Reliable transportation for covering the Chicago area

• Comfort with flexible work hours (evenings and weekends when events occur)

• Social media savvy with understanding of fitness community dynamics

• Experience in relationship-based sales or community engagement

• Ability to work independently in a field-based role

Preferred

• Established connections within the Chicago fitness community

• Prior experience in the Chicago fitness industry (instructor, community leader, etc.)

• Field sales, business development, or community management background

• Experience with CRM systems and sales processes

• Understanding of SaaS or marketplace business models

• Knowledge of event management or community operations

Compensation

• Base Salary: $45,000-$55,000 (commensurate with experience)

• Total OTE: $60,000+ plus accelerators

• Comprehensive commission and bonus structure

• Equity package included

Impact & Growth Opportunities

• Shape the future of fitness communities and social wellness in Chicago

• Build relationships with influential fitness industry leaders across the Midwest

• Drive innovation in how fitness communities operate and grow

• Create scalable solutions that impact thousands of businesses and fitness enthusiasts

• Develop expertise that spans technology, business, and fitness

• Play a foundational role in SweatPals' Midwest expansion

• Opportunity to grow into leadership positions as our Midwest presence expands

• Make a tangible impact on Chicago's fitness landscape

Benefits & Perks

• Competitive salary and equity package

• Comprehensive health, dental, and vision insurance

• Flexible PTO policy

• Field-based role with flexible scheduling

• Professional development budget

• Free access to SweatPals partner communities

• Wellness stipend for fitness activities

• Supportive team environment

• Weekly team syncs and collaborative planning

• Regular performance check-ins and coaching

SweatPals is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

To apply, please submit your resume and a brief explanation of why you're excited about connecting Chicago fitness communities through technology.