Pilot.com

Financial Planning and Analysis

• Implement rigorous problem-solving to help solve clients' operational challenges on how to manage payroll, benefits, compliance, and financial operations
• Own communication with clients regularly to provide our recommendations and manage expectations
• Bring operational best practices plus a deep understanding of back-office systems to help clients implement payroll workflows, AP/AR processes, and equity administration
• Be part of the world's preeminent operational services tech-enabled firm - a trusted partner for our clients on their most important operational decisions
• Partner with clients to help them deliver measurable and sustainable improvements in operational and business KPIs
• Keep operational projects on track with ongoing monitoring for status updates and escalation management
• Support successful compliance requirements and deadlines by tracking and ensuring timely completion
• Refine the strategies to address areas of opportunity within Pilot Financial Operations
• Recommend and contribute to process improvements to maximize accuracy and efficiency within the Financial Operations offering

Consultant, Financial Operations

• Implement rigorous problem-solving to help solve clients' most challenging operational issues on how to scale their businesses and manage their back-office operations
• Lead complex operational engagements often with multiple junior team members to deliver exceptional results
• Own communication with clients regularly to provide recommendations, anticipate their needs, and manage expectations
• Utilize operational best practices plus a deep understanding of back-office systems to help clients implement payroll workflows, AP/AR processes, equity administration, and compliance frameworks
• Research the latest developments and formulate insights into operational tools and best practices to become a strategic partner in their business growth
• Be part of the world's leading tech-enabled firm's operational services, acting as a trusted partner to our clients on critical operational decisions
• Build long-term client relationships and drive superior operational outcomes based on unique business insights
• Partner with clients to help them deliver measurable and sustainable improvements in operational and business KPIs
• Keep operational projects on track with ongoing monitoring, escalation management, and proactive problem-solving
• Support successful compliance requirements, investor discussions, and board meetings by ensuring operational excellence and providing actionable insights
• Track and evaluate key Financial Operations business initiatives, including new experiments, offerings, and process improvements
• Run ad-hoc analyses to help uncover growth opportunities or ways to scale the Financial Operations offering further
• Support new product development, new strategies, and explore new partnerships to expand the Financial Operations service line
• Mentor and guide junior team members, helping them navigate complex operational engagements and build their skills

Senior Consultant, Financial Operations

• Execute day-to-day operational tasks for our clients including payroll processing, benefits administration, AP/AR workflows, and equity grant tracking
• Apply operational best practices and support implementation of systems like Gusto, Rippling, Deel, Carta, and Bill.com
• Communicate with clients regularly to provide updates and address their operational needs
• Be part of the world's preeminent operational services tech-enabled firm - a trusted partner for our clients on their most important operational decisions
• Conduct research on operational tools and best practices required for customer service delivery
• Keep operational projects on track with ongoing monitoring and status updates
• Support successful compliance requirements by tracking deadlines and ensuring timely completion
• Execute the strategies to address areas of opportunity within Pilot Financial Operations
• Implement improvements in operational and business KPIs for Financial Operations
• Recommend and drive process improvements to maximize accuracy and efficiency within our offering

Associate, Financial Operations

• Implement rigorous problem-solving to help solve clients’ most challenging issues on how to grow their businesses and manage their finances
• Bring the latest analytical techniques plus a deep understanding of financial modeling to help clients develop financial models, budgets, and forecasts
• Develop models to track KPIs, analyze channel and SKU sales performance, enhance product margins, and forecast inventory & demand planning
• Be the world’s preeminent tech-enabled financial services firm - a trusted advisor for our clients on their most important financial and business decisions
• Become a trusted partner to clients in building the proper infrastructure to scale their business
• Advise on tactics to drive measurable and sustainable improvements in financial and business KPIs
• Keep business plans and projects on track and on budget with ongoing budget management and monitoring for variance reporting and rolling forecasts
• Support successful investor discussions and board meetings by analyzing and tracking relevant KPIs
• Support fundraising initiatives by drafting investor decks and assisting with mock pitches and term sheet comparisons
• Identify areas of opportunity within the Consumer & Retail CFO Services offering and develop strategies to address them
• Mentor new and less experienced members of the team
• Develop new products and services that are valuable to clients and can scale across the CFO Services department
• Recommend and drive process improvements to maximize accuracy and efficiency within our offering

Manager, CFO Services – CG&R

Product Designer

• Learn our platform deeply to understand the partner and client experience.
• Develop training modules that teach Local Partners how to:
• Onboard new clients using the software
• Manage client financials month-to-month
• Navigate common workflows and product features
• Create step-by-step guides, how-to videos, and visual explainers that make complex processes simple.
• Build an intuitive self-serve experience, ensuring partners can independently learn and troubleshoot.
• Collaborate with internal stakeholders (Product, Partner Ops, Sales) to align content with product updates and partner needs.
• Establish a repeatable framework for maintaining and updating training materials
• Works closely with Partner and Product teams, but largely independent in execution

Learning Experience Designer, Partner Enablement – Part-Time, Temporary

Customer Success Manager

• Proactively manage a monthly portfolio of renewing customers, collaborating with Operations and other teams to drive optimal outcomes
• Identify and address churn risks by aligning closely with Operations and supporting customer calls as needed
• Own and execute win/win contract negotiation strategies for renewals and retention
• Maintain a deep understanding of Pilot’s products and processes to recommend relevant features
• Serve as the customer’s advocate and provide internal feedback to improve product offerings and processes
• Uncover add-on or cross-sell opportunities and coordinate with product-line owners
• Maintain churn pipeline and communicate churn risks to internal stakeholders to help achieve net revenue targets
• Support financial and strategic analyses by ensuring timely off-boarding for churned customers and complete data collection
• Work cross-functionally to manage the full customer lifecycle and foster Pilot’s role as a trusted partner

Senior Customer Success Manager

Growth Marketing

• Lead creation and implementation of growth programs and strategies for the Growing SMB vertical to accelerate qualified pipeline and revenue
• Own end-to-end demand generation for SMBs from strategy to execution
• Plan and implement omni-channel campaigns across web, SEO, email, social, content, outbound, and events
• Forecast, track, and report on campaign performance and run experiments in new channels
• Collaborate cross-functionally with sales and product teams to align strategies, develop messaging and outreach tactics
• Oversee lead lifecycle including lead generation, defining MQLs, sales handoff, and nurture programs
• Build repeatable, scalable, always-on nurture programs that drive SQLs, meetings, and pipeline
• Create and utilize content that resonates with target audiences and supports demand generation

Growth Marketing Lead, SMB

Sales

• Responsible for meeting sales targets through hiring and coaching a team of Account Executives
• Consistent achievement of quarterly team sales goals and daily/weekly/monthly KPIs
• Day-to-day management of 6-8 Account Executives
• Coaching to a framework from pipeline creation to close
• Hiring to meet headcount goals
• Motivating Account Executives to learn and grow to prepare them for their next sales roles
• Understand and own information regarding Pilot’s numerous financial service offerings
• Work cross-functionally with solutions, marketing, product, and finance teams, echoing the voice of the customer and providing constructive and actionable feedback
• Work collaboratively to build and iterate day-to-day processes within the role
• Provide feedback internally to inform go-to-market strategy

SMB Sales Manager

Full-stack Engineer

• Building, testing and deploying software in a continuous manner (we deploy daily or more often)
• Working with PMs and Product Designers, and participating in product and design reviews
• Creating and contributing to technical specs and testing/rollout plans
• Working with internal customers and stakeholders to ensure we’re solving the right problems
• Mentoring and sponsoring your teammates to help them grow
• Working across teams to shape the future of engineering at Pilot
• Backend written in fully typed modern Python; frontend in JavaScript, TypeScript, and Vue.js; Terraform, Docker containers to ECS, AWS CodeDeploy, Honeycomb, Postgres

Software Engineer, Takeoff

• Build, test, and deploy software in a continuous manner (we deploy daily or more often)
• Create and contribute to technical specs and testing/rollout plans
• Work with internal customers and stakeholders to ensure we’re solving the right problems
• Mentor and sponsor teammates to help them grow
• Work across teams to shape the future of engineering at Pilot
• Support your software and services as required
• Provide scalable, efficient, high-quality infrastructure building blocks for product development
• Own the full Infrastructure stack from AWS infra to the product platform used by product engineers

Senior Software Engineer, Infrastructure

• Partner with Senior Managers or Managers to develop financial models, budgets, and forecasts
• Communicate with clients regularly to provide insights and solve their needs
• Conduct industry or company research required for customer service delivery
• Keep business plans and projects on track with ongoing budget management and monitoring for variance reporting and rolling forecasts
• Support successful investor discussions and board meetings by analyzing and tracking relevant KPIs
• Execute strategies to address areas of opportunity within Pilot CFO Services
• Implement improvements in financial and business KPIs for CFO Services
• Recommend and drive process improvements to maximize accuracy and efficiency

Associate, CFO Services

Operations

• Collaborate cross-functionally to help other teams (e.g. Revenue Operations, Finance & Accounting, etc.) execute on important recurring reporting or drive operational scale and efficiency for CFO Services and COO Services
• Serve as the primary liaison to work with the Finance Operations teams to uplevel the customers’ experiences in having both Bookkeeping and Consulting Services with Pilot
• Assist with Consulting Services' month-end close process and reconciliations between prepaid hours and billed hours
• Maintain metrics and analysis of team KPIs, and provide regular flux reporting on performance through regular business reviews for both inside and outside of Consulting Services
• Partner with the team leads and department head to make informed judgments on customer pricing, workforce planning and forecasting
• Identify trends in customers usage and advise the team leads and department head with additional revenue opportunities
• Generate, dig into and leverage data and insights to run and improve Consulting Services processes (i.e. minimize team administrative time spent)
• Support onboarding the new hires for both CFO Services and COO Services

Operations Manager, Consulting Services

Performance Marketing

• Lead creation and implementation of marketing programs and strategies to grow qualified pipeline and closed revenue in the Growing Small Business vertical
• Develop and execute comprehensive demand generation strategy aligned with company goals, product priorities, sales initiatives, and marketing objectives
• Work closely with sales teams to understand objectives, align strategies and facilitate sales-marketing alignment
• Plan and implement omni-channel campaigns across web, SEO, email, social, content, outbound, and events; forecast, track and report on campaign performance
• Run experiments in new channels and test campaign variables to optimize performance
• Collaborate cross-functionally to create compelling content and utilize content across channels to engage prospects and nurture leads
• Build omni-channel lead generation programs and oversee lead lifecycle including defining MQLs and building nurture programs
• Create repeatable, scalable, always-on nurture programs that drive SQLs, meetings, and pipeline

Senior Demand Generation Manager, SMB

• Implement rigorous problem-solving to help solve clients’ most challenging issues on how to grow their businesses and manage their finances
• Own communication with clients regularly to provide our recommendations and manage expectations
• Bring the latest analytical techniques plus a deep understanding of financial modeling to help clients develop financial models, budgets, and forecasts
• Be part of the world’s preeminent financial services tech-enabled firm - a trusted advisor for our clients on their most important financial and business decisions
• Partner with clients to help them deliver measurable and sustainable improvements in financial and business KPIs
• Keep business plans and projects on track with ongoing budget management and monitoring for variance reporting and rolling forecasts
• Support successful investor discussions and board meetings by analyzing and tracking relevant KPIs
• Refine the strategies to address areas of opportunity within Pilot CFO Services
• Recommend and contribute to process improvements to maximize accuracy and efficiency within the CFO Services offering

Manager, CFO Services

Chief Operating Officer

• Pilot launched COO Services, a first-of-its-kind offering designed to provide hands-on operational support for early-stage startups and SMBs. This role will join our founding COO Services team and will be instrumental in delivering high-impact operational work while also helping shape the infrastructure, workflows, and automation that will define the product.\n• As Principal COO Services, you’ll be responsible for directly working with customers, executing critical operational tasks (e.g., payroll, AP/AR, compliance, equity admin), and building scalable processes to make this a repeatable, high-value service offering.\n• This position reports to Cole Levin (Head of Consulting Services) and will work closely with our internal teams to develop and refine COO Services into a scalable product. If successful, this role will evolve into a leadership position as the business line grows.\n• Key Responsibilities:\n - Customer Operations Execution: Own day-to-day operational execution for early-stage startup and SMB customers, including payroll & benefits (Gusto, Rippling, Deel); Accounts Payable/Receivable; Equity Administration; Compliance & Tax Coordination; Bookkeeping & Financial Operations\n - Process & Product Development: Develop repeatable workflows, playbooks, and automation; identify AI opportunities; create internal docs; gather customer feedback; support scalability\n• Who You Are: scrappy, execution-focused operator with a builder’s mindset; 6-8+ years in operational role; hands-on experience; customer-facing; strong process-building; tech-savvy; entrepreneurial; comfortable with ambiguity.\n• Nice-to-Have: prior experience building internal infrastructure; familiarity with AI-driven tools; people management; expertise in HR/payroll/state compliance, expense management, audit-ready ops, quote-to-cash, cap table\n• Why This Role: Pioneering opportunity; blend of execution & strategy; path to leadership; work directly with founders\n• About Pilot: Pilot provides dedicated finance experts for small businesses; partners with Pilot Tax; extensive investors; etc.\n