Mid Market Sales Representative

Island · Dallas, TX

Posted today

New Business: you win brand-new customers.

Base: Not disclosed
OTE: Not disclosed
Quota attainment: Not disclosed
Posted: Yesterday

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 Island's careers page

Apply on Island →

The job

What you'd do

Find and win new customers at medium-size companies, selling software that protects their data as staff use AI. You'll hunt for most of your own leads, working in the Coppell, Texas office five days a week.

What you'd sell

Keeps company data safe while workers use apps and browsers

When a company's workers need to get their jobs done across laptops, browsers, apps, and files, the company has to keep its sensitive information from leaking out. The problem is, one stolen login or one careless click can let hackers into the whole company. Island gives workers one secure workspace for their devices, browsers, and apps, so company data stays protected while people keep working.

In plain English, from their own job posts. Something wrong? Tell me · More Security companies →

Who you'd sell to

IT and security teams at medium-size companiesIn their words: “Address the AI challenges IT and security teams face and connect our solution to their pain points.”

Where deals come from

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

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle. Ask about all five.
Time on market: Brand new.
Company hiring: 2 sales roles open, hiring at a steady pace.

Red lights

Pay. No pay listed at all.

Green lights

None spotted.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

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 percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
3.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
4.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
5.
What are the base and the OTE for this role?

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. Too much is left unsaid. Make them answer before you invest.

No pay listed at all.

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 Island ↓

Got an offer from Island? 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

Island is shaping the future of work - creating an enterprise workspace for both knowledge workers and agents - where access, security, and AI-powered productivity are built in. Our enterprise agentic control plane boosts productivity across devices, browsers, applications, networks, and data while protecting sensitive information, simplifying access, and helping enterprises scale AI safely. Behind all of that is a team of people who care deeply about their craft and want to do the biggest and best work of their careers. At Island, character and drive matter more than your resume. Backed by Coatue Management, Insight Partners, Sequoia Capital, Cyberstarts, and other world-class investors, Island is used by millions of people at some of the planet’s largest enterprises. Come build with us. Together, we’re changing how the world works. 2026 - #28 + ONLY DFW Company on the CNBC Disruptor 50 List 2025 - #1 in LinkedIn's Top Startups of 2025 2025 - #6 in the 2025 Dallas 100™ Entrepreneur Awards 2025 - Forbes Cloud 100 How We Work Note: This position is full-time five days per week in-office at our Coppell, TX headquarters (Monday through Friday). We believe collaboration and culture thrive face-to-face, and we can’t wait to welcome you to the team. What You’ll Do - Hunt: Using the latest AI GTM technology to research, engage, and chase down leads. Cold calls, LinkedIn, email, networking — if it moves the needle, you’ll try it. - Understand the problem: Address the AI challenges IT and security teams face and connect our solution to their pain points. - Own and lead: From discovery through negotiation to close, build and lead well-structured deals that set customers up to succeed. - Close: Pitch, negotiate, and close. No fluff — just real conversations that lead to contracts signed. - Team Up: Collaborate with marketing, product, and customer success to make raving fans customers. - Build trust, not just sell: The relationships you build during the sales process should be ones that last well beyond it. - Forecast clear deal notes within the CRM. The team relies on good data to make good decisions. You Might Be a Fit If - At least 1-2 years experience closing software deals with some exposure to cybersecurity. - Consistently track record surpassing revenue targets through new-business acquisition — not inherited accounts. - You hunt, you love the chase, the strategy, and the satisfaction of winning new business. - You are a naturally curious and quick learner with a reputation as a self-starter. - You master the best outreach tools and live in Salesforce. - You're a clear, confident communicator who can hold a room — discovery call, closing call, or a boardroom presentation. - Bachelor’s degree or equivalent experience — but show us your hustle. Benefits and Perks - Medical, dental, vision - Company paid Life and AD&D Insurance - Company paid STD and LTD Insurance - 401(k) with company contributions - Paid Time Off & 9 Company Holidays - In-office wellness instructor and daily lunches (for office-based roles) Physical Environment This position requires the ability to perform sedentary work, which involves exerting up to 10 pounds of force occasionally, and/or a negligible amount of force to lift, carry, push, pull, or otherwise move objects as needed. The employee will primarily operate standard office equipment and keyboards, and may require close visual acuity for tasks like analyzing data and reading extensive text. Equal Opportunity Statement Island is an equal opportunity employer. We are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to their background or protected characteristics. E-Verify Island Technology participates in E-Verify.For additional information please review the E-Verify Participation & Right to Work Poster from the Department of Homeland Security General Disclosure The job description is subject to change with or without prior notice, and a reasonable accommodation may be requested to perform the essential functions of the job. Data Privacy You can find information on how we process and protect your personal data in our Candidate and Employee Privacy Notice. For any privacy-related questions, contact us at privacy@island.io.

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