What are the responsibilities and job description for the Outside Sales Representative position at Chief of Staff?
A fast-growing specialty coffee company with a mission-driven culture and strong national presence is adding a Sales Representative to its Milwaukee team. This is a rare opportunity to inherit an existing book of business, build your own territory, and sell a product people are genuinely passionate about, all while being backed by a supportive HQ team and proven sales infrastructure.
Compensation at a glance
Base: $68–75K DOE
OTE: $85K (quarterly bonus structure)
What you'll be doing:
· Own and grow a defined territory in the Milwaukee market
· Prospect and cold outreach to coffee shops, cafes, restaurants, and hospitality groups
· Serve as a trusted advisor helping clients optimize operations, equipment, and workflows
· Manage your own schedule with autonomy, backed by a national sales team
· Hit and exceed quarterly revenue targets
What we're looking for:
✔ 2 years of B2B or outside sales — we want a hunter
✔ Proven track record hitting/exceeding quota
✔ Comfortable working independently with a remote manager
✔ Strong communicator who builds trust fast
✔ Based in Milwaukee area
Nice to have: Coffee / beverage / foodservice background, HubSpot or CRM experience, consultative selling
Why this role stands out:
· Inherit a strong existing book of business from day one
· Sell products with a real mission, specialty coffee brands built on transparent sourcing and local impact
· Small local team (3 reps) backed by a 600 person national company
· Real autonomy to run your territory your way
· Full benefits: medical, dental, vision, mileage reimbursement, and more
Salary : $65,000 - $75,000