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VP, Product Design

For the past decade, we’ve empowered thousands of teams worldwide to confidently share the Deploy button with others. Now, we’re pursuing ambitious plans to uplift entire organizations, not just the best teams, so they can confidently get changes into production.


We’re looking for a design leader to be the ambassador of our product experience, inspiring a vision of what is possible and empowering our designers to transform that vision into reality.


We’re a scale-up company, so in this role, you can expect your day-to-day to include the following:

• Think deeply about the design of human factors for individuals, teams, and organization-scale operations.

• Hold a high bar for a technical product experience that spans the web, command line, desired state code, scripts, APIs, and chat interfaces so that we can shape the most critical patterns in our design system.

• Oversee a range of customer research efforts to ensure we capture the human factors of problems, and the design considerations are represented in opportunities that product groups and teams are pursuing.

• Shape the design practice with design managers, enabling everyone to make career-defining contributions.

• Monitor the overall impact of our product experience, setting the bar for what good looks like and spotting emerging trends and issues.

• Partner with product and engineering leadership on R&D initiatives and structure.


Product designers are embedded in product groups and teams across the Australia + New Zealand and Israel + Ukraine development regions. Among them are recently introduced specialist roles such as product researcher and content designer to help us achieve a greater depth of execution.


You will be part of the R&D leadership team alongside product and engineering leadership - Colin Bowern and Michael Noonan. You will have a relationship with Paul Stovell, our founder and CEO, who is passionate about creating the best product experiences. You will work with Revenue and Marketing leaders to understand how customers land and expand. You’ll partner with People & Culture and Finance organizations to accelerate R&D and the design function.


To be considered for this role, you’ll need:
  • Cultivated a sense of what well-executed design looks like for B2B software products.
  • Experience with working with cross-functional software product teams;
  • Experience with engaging customers and cross-functional stakeholders at various levels;
  • Experience at a Director level or higher -- leading managers and principal ICs;
  • Be pragmatic and adaptable, as working in a scale-up is an ever-changing environment;
  • Have exceptional organizational and analytical skills, along with attention to detail;
  • Have excellent written and verbal communication skills


Bonus points for:
  • Experience in product expansion, where new potential paths were being explored;
  • Experience in product design of developer products with multiple interface types.
  • Worked in both a product-led and sales-led B2B product company.


Compensation:

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.


We'll discuss your compensation requirements in the initial chat.


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, and stock options. Learn more.


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] Meet a Talent Acquisition team member, where you'll learn more about life at Octopus and the role. We’ll give you a glimpse into the organization structure and how we work.


☕ Hiring manager interview

[45 Min] Meet our SVP, Product, to explore the shape of the role and the problems we're hoping to solve together.


🤩 Senior leadership approach interview

[60 Min] Meet our VP, People & Culture, to explore how you balance inspiration and accountability as a senior leader connected to our leadership code.


🧑‍💻Team interview

[90 min] Present a case study of a strategic design initiative that you’ve led. Share your initial impressions of our product. You’ll present to a panel of Design, Product, and Engineering members that you’ll work with.


🔭Founder interview

[60 mins] Meet our founding CEO to discuss how you determine what well-executed design looks like through a mix of context, design principles, and craftsmanship.


Our public employee handbook is the best place to learn more about life at Octopus. It includes our values, how we structure teamscareer progressionleave 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.


#LI-DNI

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What You Should Know About VP, Product Design, Octopus Deploy

At Octopus, we’re on the lookout for a dynamic VP of Product Design to join our remote team in Australia or New Zealand. With a mission fueled by our past accomplishments, we aim to empower entire organizations to confidently move changes into production, not just individual teams. In this key leadership role, you’ll be the ambassador for our product experience, inspiring and rallying our talented design team to bring a visionary product to life. You’ll delve deep into human factors and ensure that our design standards are top-notch across all interfaces, from web and command line to APIs and scripts. Your days will be inspiring and varied, involving customer research, mentoring design managers, and collaborating closely with R&D leaders. You’ll help shape our design practice, monitor product experience standards, and partner with various departments to enhance our growth. Your expertise in B2B software design, combined with your leadership at the director level and adaptability in a scale-up setting, will be key in steering our design efforts. Join us at Octopus and be a part of a culture that values transparency and employee growth. Here, you'll not only lead and innovate but also have the support of leaders like our CEO, Paul Stovell, in creating extraordinary product experiences.

Frequently Asked Questions (FAQs) for VP, Product Design Role at Octopus Deploy
What qualifications do I need for the VP of Product Design role at Octopus?

To be considered for the VP of Product Design position at Octopus, candidates should have extensive experience leading design teams within B2B software environments. A strong understanding of design principles for various interfaces is essential, along with a proven track record in cross-functional teamwork. Leadership experience at the director level or higher is also required, emphasizing the importance of mentoring others and driving effective design practices.

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What are the key responsibilities of the VP of Product Design at Octopus?

The VP of Product Design at Octopus will oversee design initiatives that elevate the product experience across all platforms. This includes customer research, monitoring design standards, and collaborating with product and engineering teams to influence R&D. Additionally, you'll be empowering your team to push innovative concepts while ensuring that human factors are deeply integrated into our designs.

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How does Octopus support the growth of its VP of Product Design?

At Octopus, we believe in fostering a culture of transparency and professional growth. As the VP of Product Design, you will have access to mentorship from senior leadership, including the CEO, and opportunities to influence major design initiatives. We aim to provide resources and support that allow you to thrive and impact the organization positively.

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What is the interview process like for the VP of Product Design at Octopus?

The interview process for the VP of Product Design at Octopus is designed to be efficient while informative. It includes an initial chat with a Talent Acquisition member, followed by interviews with the hiring manager, senior leadership, team members, and the CEO. Each stage focuses on different aspects of the role and assesses how candidates align with our culture and expectations.

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What benefits can I expect as the VP of Product Design at Octopus?

As a VP of Product Design at Octopus, you'll enjoy a generous benefits package that includes a minimum of 25 days of annual leave, paid sick leave, and fully paid parental leave. You'll also have transparent stock options, ensuring equity in line with your contributions. Our goal is to support a work-life balance that encourages creativity and performance.

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Common Interview Questions for VP, Product Design
How do you ensure that design decisions are aligned with business goals?

When answering this question, emphasize the importance of collaboration with cross-functional teams. Discuss how you gather input from departments like Sales and Marketing to align design strategies with organizational objectives. Share examples where your design work contributed directly to business outcomes.

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Can you describe a successful design project you led?

Highlight a project where you took the lead, focusing on the problem, your approach, and the outcome. Discuss how your leadership and design principles shaped the project and its impact on the users and the business. Specific metrics or feedback can elevate your example.

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What is your process for gathering user feedback?

Outline a systematic approach for collecting user feedback through surveys, interviews, and usability testing. Share how you incorporate this feedback into the design cycle and ensure iterative improvement, demonstrating a user-centric philosophy.

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How do you handle conflicts within a design team?

Discuss your conflict resolution strategies, emphasizing communication and collaboration. Give examples of past situations where you facilitated discussions to find solutions that honored different perspectives while focusing on the common goal of producing great design.

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What role does data play in your design decisions?

Explain how data informs your design process, from user analytics to A/B testing. Share how you use quantitative and qualitative data to justify design choices and enhance user experiences, illustrating a balance between creativity and analytical thinking.

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How do you keep your design team motivated and inspired?

Talk about techniques you use to inspire your team, such as regular design showcases, sharing industry trends, and fostering an open environment for innovative ideas. Highlight the importance of recognizing individual contributions and creating a supportive team culture.

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What do you believe distinguishes a good design from a great design?

Reflect on key elements that elevate a design, such as usability, aesthetics, and the ability to solve user problems effectively. Discuss how great design enhances user satisfaction, drives engagement, and contributes to overall business success.

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How do you balance vision with execution in design leadership?

Describe your approach to balancing high-level design vision with practical execution. Explain how you set realistic goals while encouraging innovation and iteration, ensuring your team can turn visionary ideas into actionable designs.

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How would you define the role of UX in product design?

Elucidate how UX plays a critical role in product design by addressing user needs and enhancing satisfaction. Discuss the relationship between UX and UI and how a strong UX foundation can lead to a more effective, compelling product.

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What is your approach to mentoring junior designers?

Share your philosophy on mentorship, emphasizing the importance of developing junior designers' skills through guidance, constructive feedback, and encouraging professional development. Highlight any specific practices you implement to provide support and growth.

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Full-time, remote
DATE POSTED
April 3, 2025

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