Senior Lead, Program Manager, Gusto
$150.6-218.3k
Salary dependent on location
2-3 days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$150.6-218.3k
Salary dependent on location
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 8+ years of experience in program management, operations, and/or project management roles, with a proven track record of executing large-scale, complex projects spanning multiple stakeholders and organizations
- Aptitude for understanding technical workstreams, engineering requirements, and how products/features map to operational needs for launch and change management; experience with AI-driven programs is required
- Strong understanding of service design principles and methodologies
- Stakeholder and project management mastery, with a proven ability to drive clarity, recommendations, and alignment amidst competing interests and complexities
- Insightful quantitative analysis skills, paired with strong critical thinking and sound business judgment
- Deep empathy and obsession for our small business customers
- Strong desire for continuous process improvement and a passion for driving efficiency, with demonstrated examples of leveraging AI
- Executive presence and exceptional ability to influence cross-functional, senior leaders and drive change
- Comfortable analyzing, questioning, and leveraging data to inform decisions
- Strong verbal and written communication skills, as well as data visualization and presentation skills
- Proficiency in program management software like Asana, Notion, Airtable, and JIRA
- Experience with Excel/Google Sheets and Gsuite is strongly encouraged
- When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees
What the job involves
- As a Senior Lead, Program Manager at Gusto, you will play a pivotal role in shaping the future of our customer experience within an increasingly AI-enabled environment
- This is a unique opportunity for a seasoned program manager to drive significant strategic initiatives at Gusto
- You will partner closely with executive leadership across Customer Experience, Product, Engineering, BizTech, Operational Teams, and Sales
- You will navigate complex challenges, execute large-scale cross-functional programs, and bring Gusto's strategic vision to life
- You will set the standard for how Gusto prepares the business for critical technical and operational change, ensuring our service model evolves seamlessly with new product and feature launches
- Your work will demand a deep customer obsession, strategic foresight, meticulous attention to detail, and a highly creative approach to problem-solving
- The Program Management Office (PMO) is at the heart of planning and executing Gusto's highest priorities impacting the customer. Directly supporting multiple teams, we drive impact through crystal clear priorities, robust roadmaps, and organizational rigor
- We are committed to building operational excellence and continuously improving how we deliver outstanding service experiences
- Here’s what you’ll do day-to-day:
- Strategic Program Management & Execution:
- Lead and drive high-priority, cross-functional programs for Gusto, taking full ownership for their success or failure
- Develop and manage comprehensive program and project plans, charters, and roadmaps for initiatives that interface with Product, Engineering, and Customer Experience
- Expertly identify frameworks and design principles for programs that will generate success, and propose new, creative, and effective solutions
- Collaborate with Engineering, Product & Design, and Business Technology teams to solve impactful problems across multiple initiatives, with an understanding of AI-driven solutions
- Distill complex technical concepts into clear, actionable updates for stakeholders at all levels
- Operational Readiness & Influence:
- Exhibit a systems-thinking approach to any program or decision, demonstrating a deep understanding of the interdependent relationships between teams, organizations, product/service offerings, and operational needs
- Create and implement robust AI-enabled readiness plans to prepare the business for weekly and monthly launches, ensuring smooth change management
- Shape effective reporting mechanisms and cadences for large audiences, both vertically and horizontally, providing data-driven insights and recommendations to enhance CX strategy
- Consistently demonstrate influence with executive-level stakeholders through collaboration and presentations, serving as a trusted thought partner for leaders across the organization
- Contribute to continuous improvement of team operating models, tooling (e.g., Asana, JIRA, Confluence), and reporting mechanisms
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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