Chief of Staff & PMO Leader

Sorry, this job was removed at 03:09 p.m. (CST) on Monday, Jan 06, 2025
Hiring Remotely in United States
Remote
228K-285K Annually
Fintech • Software
The Role

Innovate with purpose


At BILL, we believe in empowering the businesses that drive our economy. By replacing outdated financial processes with innovative tools, we help businesses—from startups to established brands—make smarter decisions and gain control of their operations. And we don’t stop there: we’re creating the future of financial automation so businesses can spend more time on what matters.


Working here means you become part of a vision-driven team that’s ready to tackle challenges and build cutting-edge solutions. We value purpose, drive, and curiosity—and we thrive in a fast-paced, ever-changing environment. Whether in one of our offices in San Jose, CA, Draper, UT, or working remotely, BILLders collaborate to deliver real impact for businesses that need more time in their busy weeks.


At BILL, we listen, learn, and lead—fostering collaboration and a drive for continuous growth. We’re committed to building a diverse and inclusive workplace that values each person’s unique skills and experiences. Even if you don’t meet every requirement, we’d love to hear from you—you might be just what we’re looking for, whether in this role or another.


✨ Let’s give businesses more time for what matters.

Chief of Staff & PMO Leader, CTO Organization 

Be the strategic force multiplier for our CTO and their organization!

This isn't your typical Chief of Staff role. We need a fearless and strategic leader who can optimize our CTO's impact while simultaneously building and running a world-class PMO to maximize the effectiveness of our entire CTO organization (which includes more than just engineers!).

What you'll do:

  • Be the CTO's Strategic Partner:
    • Act as a trusted advisor and sounding board, providing insights and recommendations on critical decisions.
    • Proactively identify and address challenges, anticipating needs and clearing roadblocks.
    • Drive the CTO's strategic agenda by facilitating effective decision-making, ensuring alignment with company goals, and amplifying their impact across the organization.
    • Craft compelling presentations and communications that effectively convey the CTO's voice.
  • Guide CTO Organization Towards Excellence through building a world class PMO team:
    • Establish a robust PMO framework with clear methodologies, processes, and tools that drive efficiency and accountability within a shared resource model.
    • Oversee the entire R&D project portfolio, ensuring alignment with strategic goals and optimized resource allocation across competing product roadmaps.
    • Define and implement a system for project prioritization, selection, tracking, and performance reporting that balances the needs of individual GMs with overall company objectives.
    • Drive operational excellence within engineering, including optimizing engineering operations, improving developer productivity, and fostering a culture of continuous improvement.
    • Mentor and guide program managers, fostering a culture of project management excellence and cross-functional collaboration.
  • Bridge the Gap:
    • Facilitate seamless communication and collaboration between the CTO, engineering, product, and other key stakeholders.
    • Ensure alignment on priorities, roadmaps, and execution plans.
    • Represent the CTO and engineering organization in various settings, effectively communicating their vision and achievements.


We’d love to chat if you have:



    • 12+ years of experience in a technology environment, with 5+ years in a senior leadership role.
    • Proven experience building and leading high-performing PMO teams.
    • A track record of driving organizational change and process improvement.
    • Deep understanding of software development methodologies and best practices.
    • Exceptional communication, interpersonal, and stakeholder management skills with the ability to win people over!
    • Strong analytical and problem-solving abilities.
    • A fearless approach to leadership, unafraid to challenge the status quo and drive transformation.
    • A passion for operational excellence and a drive to make a real difference.



The estimated salary  range for this role is noted below for our San Jose based role.  Our ranges for each role and job level are based on a variety of factors including candidate experience, expertise, and geographic location and may vary from the amounts listed above. The role is also eligible for a competitive benefits package that includes: medical, dental, vision, life and disability insurance, 401(k) retirement plan, flexible spending & health savings account, paid holidays, paid time off, and other company benefits.

San Jose pay range

$227,800$285,000 USD

What’s in it for you? 

Redefining how businesses automate their work is a fast-paced, exciting, and fun environment. But we also have benefits and perks to ensure the magic isn’t only experienced by our customers, but by our employees as well. 

Here is a preview of some of the amazing benefits here at BILL:

  • 100% paid employee health, dental, and vision plans (choose HMO, PPO, or HDHP)
  • HSA & FSA accounts 
  • Life Insurance, Long & Short-term disability coverage
  • Employee Assistance Program (EAP)
  • 11+ Observed holidays and wellness days and flexible time off 
  • Employee Stock Purchase Program with employee discounts
  • Wellness & Fitness initiatives
  • Employee recognition and referral programs
  • And much more

Don’t believe us? Check out our culture, benefits, and teams on our career site, LinkedIn Life, or YouTube pages.

BILL is an Equal Opportunity Employer that values diversity and inclusion. We believe our best ideas come from the unique stories, perspectives, and experiences of our team members. We welcome people of all backgrounds, abilities, and identities to bring their authentic selves and contribute to our culture.

We are committed to a transparent, inclusive hiring process that reflects our values. If you need accommodations at any stage, please contact [email protected].

Our Applicant Privacy Notice describes how BILL treats the personal information it receives from applicants.

BILL Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about BILL and has not been reviewed or approved by BILL.

  • Healthcare Strength Day-one medical, dental, and vision coverage is employer-paid at high levels and paired with HSA contributions, disability coverage, and mental-health support. Family planning and fertility resources further strengthen the healthcare offering.
  • Equity Value & Accessibility New-hire RSUs, an employee stock purchase plan with a purchase discount, and annual bonus eligibility provide long-term value alongside base pay. A clear vesting schedule improves accessibility to equity over time.
  • Leave & Time Off Breadth Flexible time off, paid holidays, and dedicated volunteer days create broad leave options. Short periods of work-from-almost-anywhere add incremental flexibility to time away and location needs.

BILL Insights

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The Company
HQ: San Jose, CA
2,753 Employees

What We Do

BILL (NYSE: BILL) is a leader in financial automation software for small and midsize businesses (SMBs). As a champion of SMBs, we are dedicated to automating the future of finance so businesses can thrive. Hundreds of thousands of businesses trust BILL solutions to manage financial workflows, including payables, receivables, and spend and expense management. With BILL, businesses are connected to a network of millions of members, so they can pay or get paid faster. Through our automated solutions, we help SMBs simplify and control their finances, so they can confidently manage their businesses, and succeed on their terms. BILL is a trusted partner of leading U.S. financial institutions, accounting firms, and accounting software providers. BILL is headquartered in San Jose, California. For more information, visit bill.com.

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