Territory Sales Representative / Restaurant Specialist - South Milwaukee, WI

SpotOn · South Milwaukee, WI

Open 5 days

New Business: you win brand-new customers.

Same role, also open in Richmond, East St Louis, MO, Long Beach, CA, Pasadena, CA, Quincy, MA, Pembroke, MA, Pasadena, TX, Gainesville, GA,

Base: $50K
OTE: $120K–$275K
Quota attainment: Not disclosed
Posted: 6d ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 3h agoon SpotOn's careers page

Apply on SpotOn →

The job

What you'd do

Sell cash register software and card payments to restaurant owners and small businesses around South Milwaukee, Wisconsin. You'll find most of your own customers through cold calling and visits.

What you'd sell

Helps independent restaurants take orders and payments in one place

When a restaurant has to take orders, ring up tables, and collect payment, there are a lot of moving parts to keep track of. The problem is, every slow or messy checkout costs money and frustrates the people waiting to pay. SpotOn makes point-of-sale systems and payment processing for independent restaurants, so orders, payments, and profit tools all work from one system.

In plain English, from their own job posts. Something wrong? Tell me · More Industry-specific software companies →

Who you'd sell to

Restaurant owners and local business owners at small businessesIn their words: “building positive relationships with local businesses & restaurant owners to help take their businesses to the next level”

Where deals come from

Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Some good signs, but there's a red light here. Get it answered before you invest.

Pay: Base and OTE both listed. Roughly a 42/58 base-to-variable split.
Transparency: Shares 1 of 5. Mentions territory. Ask about quota, attainment, deal size and sales cycle.
Time on market: Open 5 days.
Company hiring: Ramping up: posted 66 sales roles in the last 30 days. That many open roles can also mean churn. Ask how many reps are still there from last year.

Red lights

Most pay depends on commission. OTE is more than double the base. You only make the big number if you hit quota.

Yellow lights

Pay range too wide to trust. The top of the range is more than double the bottom. Ask where in that range this offer would really land.
Same job posted many times. The company has 8 or more open postings with this exact title. Could be a big build-out, could be a revolving door. Ask how many reps they hired last year and how many are still there.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percent of the variable did reps actually earn last year?
When most of the pay is variable, this is your real salary.
2.
Where in the range would someone with my background land, and why?
A wide range means the top number may not be your number.
3.
How many reps are you hiring for this, and how many from last year's class are still here?
Hiring a lot can mean growth, or people leaving.
4.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.

Before You Apply

Find out where you fit, and where you don't, before you hit submit.

Why I built it this way ↓

Most résumé tools try to make you look like a match. I'd rather help you find out if you are one.

Nothing made up.
Nothing goes on your résumé that you didn't do. If a line would need a number you didn't give me, I ask. I don't guess. On Braun Board it's checked in code, not just promised.
Curiosity before conclusions.
If the job wants something your résumé doesn't show, I ask before I assume. Plenty of sellers have done the thing and just never wrote it down.
Sorting, not selling.
Some jobs won't line up with what you've done. Finding that out before you apply isn't a loss. It's an hour back, spent on a job that fits.
No score.
A match score tells you how well you copied their words. It doesn't tell you whether you'd be good at the job, or happy there.

It's the same way I teach selling. We don't control who says yes. We do control where we spend our time, and whether everything we say is true.

Josh

1 Is the job worth it?

Ask hard questions. Some good signs, but there's a red light here. Get it answered before you invest.

Most pay depends on commission

Might be worth asking about this before you spend an hour on a tailored résumé.

See the full Braun Read

2 Where you fit

Upload once, see where you fit on any job.

What people say about working at SpotOn ↓

Got an offer from SpotOn? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Rather talk it through? Call or text me: 954-695-0844 (text)

Full posting

About SpotOn We’re not just building restaurant tech, we’re giving independent restaurants the tools to compete and win. From our award-winning point-of-sale to AI-powered profit tools, everything we do helps operators boost profit, work smarter, and keep their best people. And every solution is backed by real humans who actually give a sh*t about helping restaurants succeed. - Named the #1 Restaurant POS by G2 (Summer 2026), based on ratings from real users - Rated the top-rated point-of-sale (POS) for restaurants, bars, retail, and small businesses by Capterra users - Awarded Great Places to Work and Built In’s Best Workplaces for multiple years running We move fast, care hard, and fight for independent restaurant operators to do what they love, and love doing it. If you’re looking to make an impact with heart and hustle, SpotOn is the place for you. TERRITORY SALES REPRESENTATIVE / RESTAURANT SPECIALIST At SpotOn, you will be working in your local assigned territory and responsible for promoting our full product suite while building positive relationships with local businesses & restaurant owners to help take their businesses to the next level. We're looking for motivated individuals with an entrepreneurial spirit who excel at developing new relationships, deeply understand SMB's biggest challenges, and have the drive to make a significant impact in their local communities. Responsibilities: - Be a local representative for SpotOn in your community by offering advanced technology to local business owners that will help run and grow their businesses - Travel to and from client sites within a designated geographical territory to prospect, build relationships, and sign up new local business owners and merchants - Manage the full sales cycle from start to finish with a growing portfolio of clients - Hit sales targets, with a particular focus on selling software & point-of-sale solutions along with payment processing - Work closely with our extended Sales Support team to help reach your monthly sales performance goals Qualifications: Research shows that women and members of underrepresented groups tend to apply to roles only when they check every box on a job description. We encourage you to apply if you meet the majority of our qualifications and if this role is aligned with your career trajectory. - 2+ years of B2B sales experience with an emphasis on small business owners, merchants, and restaurants - Proven track record delivering against sales goals with a metrics-oriented, need-to-win attitude - Excellent cold calling, prospecting, and territory buildout experience - Proficient in Salesforce as a CRM is a plus - Maintain and manage the client relationship in collaboration with our internal support teams to ensure the success & satisfaction of your customer portfolio - The ability to learn technology basics and apply them to business situations - Ability to embrace feedback and hold yourself accountable Benefits: - At SpotOn, we put people above everything else. We’re known for our innovative software and technology solutions, but we stand out because of the hardworking humans behind the tech. We can’t take care of our clients without taking care of our employees first, and that’s why we invest in your wellbeing with a competitive benefits package designed to support your health, family, and future: - Medical, Dental, and Vision Options: Nationwide plans to fit your personal healthcare needs. - HSA with Employer Match: High-deductible health plan enrollees receive an annual company contribution to their Health Savings Account - Company-Paid Life Insurance & Disability - 401(k) Retirement Savings & Annual Employer Match - Restricted Stock Units (RSUs) - Pre-Tax Commuter Benefits - Paid Parental Leave - Paid vacation, 10 company holidays (including 1 floating holiday), sick time, and volunteer time off - Monthly cell phone and internet stipend - Education reimbursement up to $2,000 per calendar year to assist with your professional development - Employee Resource Groups to build community and inclusion at work Compensation: - A full-time, W2 position with an annual salary of $50,000 and total on-target earnings of up to $120,000-$275,000. Total on-target earnings are inclusive of base salary and commission potential. - Please note the earnings listed are just one component of a competitive compensation package, which includes company RSUs. - Commissions will be paid weekly for new accounts signed, bonuses earned for hardware and implementation, monthly production bonuses, and customer retention. - Offers will be reflective of the candidate’s location and experience. Travel and Work Environment: - This role requires regular travel to client locations onsite for up to 6 hours per day, and the employee must have reliable transportation. Where driving is required, employees must hold a valid driver’s license, maintain a driving record that meets company standards, and have reliable transportation with active auto insurance. In dense urban territories (for example, Manhattan, NY), travel is typically by public transit or on foot, and driving may not be required. Working hours may vary based on client needs. The employee must be able to travel to and enter customer sites, which may include restaurants, retail spaces, warehouses, and construction environments, and to stand and walk for extended periods during site visits. Sites may not be controlled by the company and may have variable temperature, noise, lighting, and accessibility. The employee must be able to lift and carry items such as a laptop, demo equipment, product samples, or marketing materials weighing up to 10 pounds, including loading and unloading them from a vehicle. #LI-REMOTE We will never ask candidates to pay fees, purchase equipment, or share sensitive personal or financial information during the hiring process. All legitimate communication from our recruiting team will come from an official company email address (@spoton.com http://spoton.com). If something seems suspicious, please contact us at careers@spoton.com. SpotOn is an equal employment opportunity employer. Qualified candidates are considered for employment without regard to race, religion, gender, gender identity, sexual orientation, national origin, age, military or veteran status, disability, or any other characteristic protected by applicable law. For U.S. based roles, work authorization in the U.S. is required. Visa sponsorship is not available for this role. SpotOn is an E-Verify company.

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