Director, Enterprise Sales- Americas

Octopus Deploy sets the standard for Continuous Delivery, empowering software teams to deliver value in an agile way. Over 4,000 organizations globally – including Ubisoft, Xero, Stack Overflow, NASA, and Disney – rely on our Continuous Delivery, GitOps, and release orchestration solutions.

Founded in Australia in 2012, our team of over 300 Octonauts now spans the globe. We combine high growth and big ambitions with a sustainable, balanced working environment. Our revenue has grown consistently between 30–50% every year for the past 8 years, and we’ve been profitable for 10 out of the past 11 years. Octopus now provides the industry's most comprehensive Continuous Delivery solution for organizations operating at scale.

We’ve been remote-first since 2015 and work with an uncommon level of transparency. You can read our public handbook to learn how we work. We have a transparent approach to compensation that ensures people doing the same work with the same skill get paid the same, with well-defined career pathways. We foster a supportive, collaborative, and high-trust environment. We leave our job titles at the door and focus on doing what’s best for our customers and team. Our leaders never shy away from answering the tough questions at our all-hands calls or in 1:1s. We conduct interviews and onboarding virtually as part of being a remote-first company.

The Director of Sales is a key member of our sales leadership team and is responsible for generating revenue across a specific geography or territory. We are looking for highly motivated sales leaders who will mentor and coach Enterprise Account Executives.

To help our teams work together effectively, this remote position requires you to be located the United States or Canada.

What You'll Do:

Responsible for leading the sales team to meet and exceed sales goals.
Training sales reps on various techniques that are needed to reach set KPIs.
Identify where improvements can be made and develop sales plans and strategies to achieve sales goals.
Focus on new sales and account management for our enterprise segment prospects and customers.
Develop and maintain exceptional relationships with clients.
Proactively identify customer needs/pain points and direct sales reps to create account growth plans.
Collaborate with engineering and product management as the voice of the customer for product-related needs and positioning with strategic accounts.
Work collaboratively and cross-functionally with various teams to help shape Octopus Deploy’s products and solutions to meet customer needs (e.g., marketing, success, product, legal, etc.).
Geographic focus on US Central and West region.

Your Background:

10+ years of sales experience and 5+ years of people management experience.
Experience leading a sales team in a high-growth technology environment covering enterprise or strategic accounts.
Familiar with MEDPICC and other selling methodologies.
Ability to train and coach a high-performing sales team as well as lead strategic opportunities individually when necessary.
Ability to build strategic executive relationships with customers and industry thought leaders.
Ability to work cross-functionally, particularly with Product and Marketing, to develop product functionality and create effective marketing plays to win clients.
Must have prior DevOps, CI/CD, or SDLC tooling sales experience ideally in a pre-IPO company.
Experience in scaling high growth technology companies not only in sales but operations, marketing, product etc to $100M and beyond in annual recurring revenue.
Some travel will be required (<25% of the time)

Octopus has an internally open and transparent system for compensation. Any Octonaut can view the compensation for any role at any level. This ensures people doing the same work with the same skill get paid the same.

The compensation for this role is:

Director Level

People in this role may be expected to participate in an on-call program that pays an additional 5% on top of the base salary. You can opt out of on-call rotation.

Benefits include a minimum of 25 days annual leave, up to 10 days of paid sick and carers leave, 12 weeks of fully paid parental leave with flexible return options, generous health care (100% individuals, 75% dependents), dental and vision, 401K matching, pension contributions of up to 5%, and stock options. Learn more.

Interview Process

Below is the interview process you can expect for this role. We know interviewing can seem daunting, but rest assured we designed our interview process to move quickly while still getting you all the information you need.

👋🏼Initial chat [30 min]

Talent acquisition screen: Meet with your Talent Acquisition team and get a feel for what it would be like to be an Octonaut!

🧑‍💻Hiring manager chat [45–60 min]

Hiring manager chat: Designated time to chat with the hiring manager. This is a great opportunity to get to know each other. You should expect the hiring manager to ask questions about your professional background and goals. We welcome any questions you may have for us!

🎉Panel interview [60–90 min]

Final round chat: In this final round call, you meet cross-functional team members. You can expect a mix of leaders and individual contributors to join the chat. By the end of this call, you should have a great idea of what it’s like to work at Octopus. We should also have a great idea of what it would be like to have you on the team! We’ll ask any final questions and encourage you to do the same.

Our public employee handbook is the best place to learn more about life at Octopus. It includes our values, how we structure teams, career progression, leave and benefits, and much more.

If you're enthusiastic about this position, even if you don’t meet all the criteria above, we wholeheartedly encourage you to submit your application. Our talent team is in-house, and we recognize that every individual brings something unique. We take the time to review every application and consider how you might add to the team.

We know your time is precious. If you apply, we promise to update you at least once per week about the status of your application and to give you clear expectations for each step in the journey.

Important Notice About Recruitment Scams

Please be aware that individuals and organizations may attempt to scam job seekers by offering fraudulent employment opportunities under the name of Octopus Deploy or Codefresh by Octopus Deploy. These scams may involve fake job postings, unsolicited emails, text messages, or other communications claiming to be from our recruiters or hiring managers.

Octopus Deploy will never:

• Ask for sensitive personal information, such as credit card details, bank account numbers, or other financial information during the recruitment process.

• Request payment, fees, or purchases from job seekers.

• Send checks for equipment purchases prior to employment.

Official Communication Channels:

All communication from Octopus Deploy recruiters or hiring managers will come from official email addresses ending in @octopus.com. If you receive messages from other domains (e.g., name.sr.octopus.com or generic addresses like @yahoo.com), these are not from Octopus Deploy.

If you are unsure about the authenticity of a communication claiming to be from Octopus Deploy, do not provide any personal or financial information and contact us immediately at recruitment@octopus.com.

Reporting Fraud

If you believe you have been a victim of a recruitment scam, please report it to the appropriate authorities:

United States: Federal Trade Commission (FTC)

Europe: European Anti-Fraud Office (OLAF)

New Zealand: NetSafe

Australia: Australian Cyber Security Centre (ACSC)

Signs of a Recruitment Scam

Be vigilant about the following red flags:

• The sender uses email domains that do not end in @octopus.com (e.g., name.sr.octopus.com or generic addresses like @yahoo.com or @hotmail.com).

• Poor spelling and grammar in emails or official-looking documents.

• Requests for payment, financial details, or fees to proceed in the hiring process.

• Receiving a check and being asked to deposit it for equipment purchases before employment.

• Contacting you through informal channels such as WhatsApp, particularly in the United States.

• Pressure to act quickly or threats of losing the opportunity if immediate action is not taken.

We take fraudulent activities seriously and are committed to ensuring the integrity of our hiring process. Thank you for helping us protect our community and future Octonauts!

[Note to Search Firms/Agencies]

Octopus Deploy does not compensate search firms for unsolicited assistance unless they have a written search agreement with Octopus Deploy and the requisition is position-specific. Any resumes, curriculum vitae and other unsolicited assistance from search firms that do not have a written search agreement or position-specific requisition submitted to any Associate of Octopus Deploy will be deemed the sole property of Octopus Deploy and no fee will be paid in the event the candidate is hired by Octopus Deploy.

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Why Octopus Deploy

If you join Octopus, you’ll be joining a high trust, remote-first team that helps over 150,000 people around the world to deliver working software to production.

We’ve been around since 2012 and we’re used by over 25,000 companies, including ASOS, Xero, StackOverflow, NASA and Disney.

Growing, sustainable company

We’re profitable and long-term oriented. And yet we’re growing quickly. It’s a unique opportunity to join a growing company without all the craziness. With that growth comes all kinds of opportunities for career progression and professional and personal development.

What to expect

What’s it really like here? We’ve made our internal handbook public, so you can see for yourself. It will answer many of the questions you might have.

Read our Handbook

Benefits & perks

Impact

Trust and autonomy to do the best work of your life, in work that makes a meaningful difference.

Competitive salary

Along with a pro-active salary review and feedback system.
Learn more.

Opportunities

As we grow, new opportunities to learn, advance and contribute are continuously opening.

Laptop & home office

Choose your own laptop and home office program.
Learn more.

Health & dental

Excellent health care, dental and vision.
(US only)

Retirement

Generous 401K / pension retirement plan matching.
(US & UK only)

Work/life harmony

No crazy hours or arbitrary deadlines.

Parental Leave

Paid parental leave for primary & secondary carers.

Don’t see a role you’re interested in?

If you share our core values but none of the roles above seem quite right, but you think you can bring something unique that might help, we’d love to hear from you. Just talk to us.