Braun Board

Enterprise Account Executive (DevOps)

Rewind · Remote · Canada

Full health. Just posted.

New Business: you win brand-new customers.

Base
C$130K–C$170K
OTE
Not disclosed
Quota attainment
Not disclosed
Posted
4h 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 2h agoon Rewind's careers page

The job

What you'd do
Sell a service that backs up cloud tools like Jira and GitHub to very big companies, mostly to their top technology leaders. You'll win new customers and find many of your own leads, along with leads from partners and free trials.
What you'd sell

Keeps backup copies of work stored in Jira and GitHub

When a software team keeps its work in cloud apps like Jira or GitHub, it has to make sure a copy of that work is always safe somewhere. The problem is, that work is critical to the business, and losing it can grind projects to a halt. Rewind backs up the data in those cloud apps, including Jira, GitHub, Confluence and Shopify, so the company can get its critical data back when something goes wrong.

In plain English, from their own job posts. Something wrong? Tell me · More Developer & IT tools companies →

Who you'd sell to
Software teams and heads of IT, technology, security at big companiesIn their words: “You will interface with DevOps and Technology leaders within the office of the CTO, CIO and CISO”
Where deals come from
A mix. Some leads come to you, some you find yourself.

The Braun Read

Ask hard questions

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

Pay
Base is listed but not OTE. Ask what the variable is and how many people hit it.
Transparency
Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market
Brand new.
Company hiring
This is their only open sales role.

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. 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. 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. 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. 4.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  5. 5.

    What's the OTE, and what did the median rep earn last year?

    Base is what you're guaranteed. OTE and the median show the upside.

  6. 6.

    Why is this role open? Did someone leave, or is it new?

    New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

  1. 1.

    Can I see the full comp plan in writing, including clawbacks and accelerators?

    What's in writing is what gets paid. Read it before you sign.

  2. 2.

    Can I see the actual comp distribution for the team last year, not just the OTE?

    The spread shows what most reps really take home. OTE is just the target.

  3. 3.

    I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?

    Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

Going for your first AE role? Get the free interview kit → 24 questions, what good and bad answers sound like, and an offer comparison sheet.

Got an offer from Rewind? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
+ Add offer details (optional)

Goes straight to my inbox. I never share it with employers or recruiters.

Full posting
Rewind is a service that protects the critical data that powers businesses of all sizes. Our focus is on backing up data that lives in the cloud - in apps like Jira, GitHub, Confluence and Shopify. We are backed by Insight Partners, Inovia, Bessemer and Atlassian Ventures and are proud to be recognized as one of Canada's 50 fastest growing technology companies (2023 Deloitte Fast 50 https://www.deloitte.com/ca/en/about/press-room/deloitte-canada-announces-its-annual-technology-fast-50tm-program-winners.html). We invite you to read our startup story https://rewind.io/blog/why-we-started-rewind-backups/ to learn where we came from and where we’re going. Read about our mission, story and values here https://rewind.com/about-us/. To find out more about our perks, click here https://rewind.com/careers/#:~:text=Working%20at%20Rewind%20has%20its%20perks. Some of our Blogs might help you get a better understanding of what we do here. You can find them all here https://rewind.com/blog/. Thriving at Rewind: We embrace the fast-paced, ever-changing nature of startup life. If you love working with speed, agility, and creativity, you’ll feel right at home here. Here's what it takes to succeed with us: - Team-First Mentality: We put teamwork at the core of everything we do, believing that we are better when we are together. Success is shared, and when the team wins, we all win. - Performance-Driven Mindset: We are proactive, goal-oriented, and focused on delivering tangible, high-quality results. We go beyond meeting expectations - we aim to exceed them. - Flexible Work-Life Approach: We encourage balance and understand the need to recharge. While we stay agile for urgent needs, we make sure there's time to recover and enjoy life. - Customer Centricity: Our commitment to customers shapes everything we do. We listen, build relationships, and innovate - from our dedicated customer support team to our engineers, everyone at our company is focused on solving problems that matter most to our users. - Taking Initiative: We value ownership and proactive problem-solving. We encourage team members to think creatively, take ownership, and lead improvements. Your ideas and actions drive our success. - We Make Time for Fun: We work hard and make time to enjoy the journey. It’s not just about hitting milestones—it’s about making the experience rewarding along the way. The Enterprise Account Executive will own the full sales cycle from discovery through to close, primarily focused on selling Rewind’s DevOps (Jira, Confluence, BitBucket, GitHub & Azure DevOps) Backup & Resilience platform. You will interface with DevOps and Technology leaders within the office of the CTO, CIO and CISO, and work tightly with ecosystem channel partners. This role combines both inbound and outbound sales. You’ll benefit from a strong pipeline of opportunities generated through an industry leading Technology and Solution Partner program, free trials via our SaaS marketplace listings (Atlassian, GitHub, etc.) and traditional demand channels. Supplementing these leads through your own opportunity creation through targeted prospecting and partner relationship development will be key. With a major Atlassian cloud migration shift (Atlassian Data Center End of Life https://www.atlassian.com/enterprise/data-center) already underway, you’ll be well-positioned to capture a massive market opportunity, as some of the largest companies in the world transition their business critical applications to the cloud, ultimately, requiring the protection that Rewind provides. WHAT YOU’LL DO SALES PROCESS MANAGEMENT - Own the entire sales process from discovery through to close, including infosec and legal reviews - Collaborate with Sales Engineering to deliver impactful demos, guided trials & POCs - Keep opportunities updated daily in Salesforce for visibility and forecasting accuracy. AI use is encouraged! New business generation - Drive net new revenue by closing new enterprise customers - Deploy creative outbound prospecting strategies to generate pipeline from net-new target accounts - Build relationships, with the support of our Partnerships team, within top Solutions Partners to identify and generate interest from new prospects Market engagement & feedback - Support the Product team with feedback from prospects to help shape product direction - Share learnings with the broader Sales team to improve our collective approach - Attend industry events and meet with customers on-site as needed WHAT YOU’LL BRING - 5+ years of B2B SaaS closing experience with consistent quota achievement - Strong discovery and closing skills, with a naturally curious approach to customer needs - A motivated, creative mindset - finding new paths when faced with obstacles - Comfort with ambiguity and the ability to bring structure to fast-changing environments - Nice to have: experience selling to CTO/CIO/CIO, DevOps or technical buyers Compensation Philosophy The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process. In some cases, we’re open to hiring at a higher level for the right person and are committed to paying competitively and fairly. If your experience is closer to an earlier career stage, we may still consider your application. In that case, we would evaluate the role at a different level within our levelling framework. Pay is just one part of the overall compensation at Rewind. Why join Rewind At Rewind, you’ll help shape the future of data protection for thousands of businesses. We’re performance-driven, innovative, and not afraid to challenge what’s possible. You’ll join a team that values trust, accountability, and respect for people’s time — and encourages every employee to experiment, think critically, and grow. We support innovation through experimentation — including smart use of AI tools — and believe the best ideas come from those who aren’t afraid to push boundaries. How Rewind Will Support You We know that enjoying the journey is just as important as reaching our goals. We work hard to create a positive, inclusive environment where fun and laughter are part of our everyday routine. We also offer a variety of benefits to support your success both at work and in your personal life which includes but is not limited to:  - Flexible work hours - Employee stock options - Health benefits - 3 weeks vacation - 7 life leave days - 2 Level Up days for professional development - 1 volunteer day - Summer Fridays and office closed during the holiday break in December - Paid parental leave - $2000/year wellness/home office allowance - $5000/year professional development allowance Rewind is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career. We value how each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. We strongly encourage candidates of all different backgrounds and identities to apply. AI Usage Our recruitment process may include the use of artificial intelligence–enabled tools to help manage and review applications efficiently. These tools assist our team, but hiring decisions are ultimately made by human reviewers.
Apply →