Sales Performance Coach Midwest

Clipp; Chicago (IL); Remote; USD 70,000 - 110,000; Full time

Benefits offered by this job

Health benefits

Dental & vision

Remote work options

Travel opportunities

Job summary

Clipp is seeking a Sales Performance Coach to train field teams across the Midwest, with remote work and up to 70% travel. You’ll deliver hands-on coaching to new hires and experienced reps, helping them close more deals and grow their careers.

You’ll partner with the Sales Training & Development Team to roll out strategies, share real-time field insights, and tailor programs for local markets. A road‑warrior mindset, clear communication, and coaching excellence are essential to drive results.

Qualifications

• 5+ years in sales in advertising, marketing, or local business solutions.
• 2+ years in coaching, mentoring, or training roles (bonus if field-based).
• Familiarity with CRM tools, sales training platforms, and analytics.

Responsibilities

• Deliver hands-on, in-field coaching to sales reps and leaders.
• Provide one-on-one coaching to new hires to accelerate success.
• Take top reps to the next level with personalized coaching and insights.
• Host sales workshops, role-plays, and sessions to boost engagement and results.

Skills

Sales expert

People motivator

Road warrior

Creative problem-solver

Strong communicator

Tools

CRM tools

Sales training platforms

Analytics

Job description

Sales Performance Coach - Field-Based Coaching to Build Winning Sellers!

Remote – Travel Required (Up to 70%)

Are you passionate about helping others succeed and thrive in a fast-paced sales environment?

Job Type: Full-time

As a Sales Performance Coach in our Midwest Region, you’ll play a key role in getting new sellers up to speed and helping experienced reps sharpen their skills. Through hands‑on, in‑field coaching, you’ll guide our sales teams to greater success, ensuring they have the tools and confidence to close deals and grow their careers.

Applicants must be located in one of the following markets to be considered: Chicago, IL; Detroit, MI; Milwaukee WI; Minneapolis MN; Cleveland or Columbus OH.

This role is all about impact—you’ll be working directly with sales reps and leaders to refine their approach, drive results, and level up our team. In doing so, you’ll directly support our mission of delivering effective marketing solutions that help small businesses grow and consumers save, making a real difference in local communities. If you love mentoring, thrive on collaboration, and enjoy being on the road, this is the perfect opportunity to take your coaching skills to the next level!

Coach & Develop Talent

• Deliver hands‑on, in‑field training to sales reps & leaders.
• Provide one‑on‑one coaching to new hires to accelerate their success.
• Take top reps to the next level with personalized coaching and expert insights.

Collaborate & Innovate

• Work closely with our Sales Training & Development Team to roll out game‑changing strategies.
• Share real‑time field insights to help shape future training programs.
• Bridge the gap between corporate strategy and local market execution.

Empower Sales Leaders

• Partner with senior sales leadership to create custom training plans for growth‑focused markets.
• Equip sales managers with coaching tools & techniques to inspire and guide their teams.
• Mentor new managers to sharpen leadership skills and build winning teams.

Drive Sales Performance

• Lead by example—prospect, pitch, and close deals alongside sales reps.
• Share best practices for selling our direct mail and digital solutions.
• Host sales workshops, competitions, and role‑playing sessions to boost engagement and results

Who You Are

• Sales Expert – You’ve thrived in a sales‑driven environment, ideally in advertising, marketing, or local business solutions.
• People Motivator – You love coaching, training, and inspiring teams to succeed.
• Road Warrior – You’re ready to travel up to 70% across the U.S.
• Creative Problem‑Solver – You can adapt your coaching style to fit different markets and personalities.
• Strong Communicator – You can command a room, deliver engaging training, and provide constructive feedback.

Why Join Us

• A fast‑growing company with a mission to help small businesses thrive.
• Competitive salary + performance‑based bonuses—your impact is rewarded!
• Professional development opportunities to grow your career.
• Comprehensive benefits—health, dental, vision, and more!
• Innovative, people‑first culture where your ideas matter.

What You’ll Bring

• 5+ years of sales experience (direct marketing, advertising, or similar industries preferred).
• 2+ years in a coaching, mentoring, or training role is preferred (bonus if field‑based!).
• A strong track record of meeting or exceeding sales targets.
• Familiarity with CRM tools, sales training platforms, and analytics.
• A growth mindset—always looking to improve and help others do the same.
• A valid driver’s license & willingness to travel up to 70%.