Chief of Staff - Technical at Octane

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Company Overview

Octane is late-stage Fintech startup that is disrupting lending in the passion purchase segment. With a mission to connect people to their passions and an initial focus on the $21B powersports market, Octane is leading the segment with its promise of speed and ease and digital capabilities (through automated underwriting, innovative credit products, and financing through our in-house lender Roadrunner Financial, editorial brands like, gaining traction quickly with customers, growing originations more than 3X year-over-year. Because we’re the platform and the lender, we have both high growth and positive unit economics - rare for a fintech. Octane recently closed its Series D raise and is in the midst of expanding into adjacent verticals beyond powersports in the passion purchase category.

The Role

We are looking for an experienced, self-driven Chief of Staff or an exceptional candidate looking to grow into this role. You will report directly to the Chief Technology Officer (CTO) of the company, working closely with him and across his leadership team and that of his c-suite counterparts to drive relentless focus on improving the experience for execution, with empathy for the people and for Octane’s customers. You'll thread the needle across multiple teams and support the CTO in delivering results and holding teams accountable.

To be successful in this strategic and technical role, you must be comfortable working with engineering teams, product teams and key business partners (including HR, recruiting, and finance). You will be driving continuous process improvement and simplification, enabling the team to succeed in the highly dynamic world of cloud computing, while removing obstacles. You will drive our efforts to identify key initiatives and investment areas, support the short-term and future strategy in alignment with Octane’s mission and values, and track execution and operations across the org.

In this role you will also deep dive on critical experiential issues faced by the business. Actively seeking out opportunities to fine tune and redefine our processes will be core to everything you do, as well as demonstrating leadership and expertise in understanding the underlying user experience issues and technology of our systems. The role will evolve as business needs change but will start out covering below functional areas as key responsibilities.

Key Responsibilities

  • Operations: As Chief of Staff, you will drive the rhythm of the business, including reviews, leadership meetings, strategy sessions - thinking holistically and strategically about key business processes, organizational effectiveness and efficiency, employee engagement, and organizational communications.
  • Communications: You will actively establish the communication program for the CTO by defining talks, narratives, and engagements with staff and internal stakeholders.
  • Project management: Tracking high priority initiatives for the CTO and identifying any obstacles, communicating initiative status to the executive, pulling in other executives or team members as necessary, connecting teams that are working on similar initiatives, pulling together and managing project teams that require input from multiple areas within the company.
  • Cultivate Relationships: Success in Engineering is dependent on cross-functional and cross-organization relationships; good relationships start with empathy and trust. You will identify stakeholder relationships to build and effectively partner with to facilitate the success of your role and the organization’s mission.
  • Culture and People: You will work closely with the CTO, CPO, HR and the leadership team to identify, analyze, and develop strategies to improve organizational health for employees as indicated by employee feedback, from personal observation (requires a good pulse on the org), or other employee listening systems. You will work closely with the leadership team and HR team on implementing an overall morale strategy.
  • Strategic Initiatives: You will create and implement accurate strategic plans and develop success metrics. You will be on point for the communication approach for special initiatives and projects developed throughout the year.
  • Budgeting & Hiring: You will elevate our partnership with Recruiting to ensure our organization attracts the best and brightest candidates and any openings are filled quickly meeting organizational hiring objectives. You will hold hiring managers accountable for ensuring a positive onboarding experience.


  • 10+ years’ experience as senior software leadership, product management, technical project management or similar role in technology industry
  • Proficiency with office productivity suite (similar to PowerPoint, Word, etc.)
  • Demonstrated ability to effectively communicate (oral and written) at all levels across an org
  • A highly Collaborative mindset (excellent technical and non-technical stakeholder management skills)
  • Experience using agile software development practices and associated tooling
  • Proficiency with progress tracking tools (similar to Jira, Trello, Project, etc.)
  • Nice to have: Bachelor’s/Master’s degree in business, marketing, engineering, computer science or related field
  • Nice to have: People management experience


  • Robust Health Care Plans (Medical, Dental & Vision)
  • Up to 5 weeks PTO (self-managed)
  • Generous Parental Leave
  • Retirement Plan (401k) with Company contribution and Match
  • Educational Assistance/Tuition Reimbursement up to $3K/year 
  • Powersports Safety Benefit: reimbursement of up to $500/year for the purchase of any powersports safety equipment
  • Life Insurance (Basic, Voluntary & AD&D)
  • Short Term / Long Term Disability & Life insurance
  • Team Activities (remotely)
  • Monthly company gift
Octane Lending is an equal opportunity employer committed to providing equal employment opportunity without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, or any other protected status with respect to recruitment, hiring, promotion and other terms and conditions of employment.



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Candidate Location Eligibility:
New York City, NY

Technology we use

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An Insider's view of Octane

How would you describe the company’s work-life balance?

At Octane, work and life have never felt at odds with one another. When life happens or we need a moment, there is always understanding built on trust and respect. Then at work, once the storm has passed, shared company values and goals align and motivate everyone to bring their whole selves to work.

Caroline Ho

Staff Engineer

How do you collaborate with other teams in the company?

Today, we use a tool that emulates the look and feel of our physical office and gives users the ability to easily hop in between desks and rooms to talk to each other. With us going back to a hybrid model, we'll continue using tools like this so we allow for organic, serendipitous discussions, similar to catching someone in the hallway for a chat.

Kevin Park

Director, Product Strategy & Data

How has your career grown since starting at the company?

I have been at Octane for only a year but I have seen exponential growth in my career. The leadership at Octane has always motivated me and provided me with opportunities to present my work and given me constructive feedback to hone my skills. Octane’s culture makes employees feel valued and instills the confidence to work to their full potential.

Geetika Chawla

Dealer Risk Manager

How do you make yourself accessible to the rest of the team?

To make myself accessible, I engage in 1:1s with various members of the team, have a public calendar so people can throw on a meeting if there is ever something they want to discuss, do strategy sessions several times a year, host an all-hands every month, and attend company happy hours.

Jason Guss


What are some things you learned at the company?

At Octane I’ve learned that small, scrappy teams of highly motivated individuals can accomplish big things. And that world-class products require both focus and patience to build. We’re just as proud of the things we say “No” to, as we are of the products we ship that delight consumers and make life easier for recreational dealers.

Evan Coates

Vice President & General Manager, Consumer

What are Octane Perks + Benefits

Octane Benefits Overview

Benefits Include:

Robust Health Care Plans (Medical, Dental & Vision)
Up to 5 weeks PTO (self-managed)
Generous Parental Leave
Retirement Plan (401k) with Company contribution
Educational Assistance/Tuition Reimbursement up to $3K/year
Powersports Safety Benefit: reimbursement of up to $500/year for the purchase of any powersports safety equipment
Life Insurance (Basic, Voluntary & AD&D)
Short Term / Long Term Disability & Life insurance
Team Activities (remotely)
Monthly company gift

Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Team owned deliverables
Group brainstorming sessions
Pair programming
Open office floor plan
Diversity Employee Resource Groups
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Employees can contribute up to $2,750 per year and use these funds for eligible medical, dental and vision expenses.
Disability Insurance
Dental Benefits
Octane's dental plan covers 100% of preventative care costs!
Vision Benefits
Health Insurance Benefits
70% company contribution
Life Insurance
We cover you with a life insurance policy valued at 1x your salary.
Pet Insurance
Retirement & Stock Options Benefits
We make an annual contribution of 3% of your prior year's W2 earnings, whether you contribute to your 401k or not.
Company Equity
Match charitable contributions
We will match each charitable contribution that ranges from $25 - $500.
Child Care & Parental Leave Benefits
Generous Parental Leave
Employees may receive paid time off up to a maximum of 4 weeks birthing & recovery and/or 12 weeks bonding leave for any birth, adoption or placement event in a rolling twelve (12) month period.
Remote Work Program
Vacation & Time Off Benefits
Generous PTO
Exempt employees are encouraged to take at least 2 weeks, but can take as many as 5 weeks of vacation time per year.
Paid Holidays
Paid Sick Days
New York and Texas employees receive additional sick time
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Stocked Kitchen
Some Meals Provided
Happy Hours
Professional Development Benefits
Tuition Reimbursement
Octane will reimburse 90% of approved tuition, fees and other expenses, up to a maximum of $3,000 per year, incurred by an employee for continuing education through an approved program.
Lunch and learns
Promote from within

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