Senior Level Director of Flight Operations Jobs
Senior level director of flight operations jobs place experienced aviation leaders in charge of regulatory compliance, operational strategy, and the cross-functional teams that keep flight programs running safely at scale. Hiring concentrates across Banking & Financial Services, Technology & Software, and Aerospace & Defense, with employers like Stripe, Amazon, and BNH actively hiring at this level now.
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Avalara is transforming tax compliance into a seamless, automated digital experience. Within our Micro & Emerging Business unit, we are building a unified self-serve compliance platform for small merchants and lodging operators by bringing DAVO and MyLodgeTax together.
As a Senior Program Manager, you will lead the cross-functional operations of this flagship initiative. You will drive alignment, accountability, and execution across dedicated engineering teams, central platform groups, business development, billing systems, and shared services. Reporting to Evan Wright (VP & GM, SMB Business), this role gives you startup-style agility and scope backed by the data, customers, and infrastructure of an established global SaaS leader.
Lead program delivery. Own the integrated plan, milestones, and critical path for the DAVO and MyLodgeTax consolidation, including the platform rebuild, customer migration, and security and compliance deadlines.
Run the cross-team operating model. Set up operating rhythms, dependency maps, and clear service agreements with engineering, central platform, business development, filing operations, and corporate systems teams.
Drive billing and systems work. Coordinate roadmaps and delivery for card and ACH checkout, self-serve pricing and quoting, HubSpot, ERP integrations, and the APIs underneath them.
Align partner integrations. Coordinate timelines across POS and property-management integrations, marketplace apps, and integration partners so customers can sign up and onboard without talking to sales.
Give executives clear visibility. Build dashboards tracking self-serve conversion, support volume, and acquisition economics, and write decision memos that make trade-offs easy to act on.
Modernize how programs run. Use AI tools for status updates, risk detection, and documentation, and help CPMO turn what works here into playbooks for the rest of Avalara.
#LI-Remote
What Your Responsibilities Will Be:
Lead the end-to-end go-to-market strategy, campaign planning, and execution for DAVO to accelerate merchant acquisition, trial sign-ups, and active user growth.
Own marketing initiatives across app marketplaces, POS ecosystems (e.g., Clover, Square, Toast, Shopify, and others), and merchant-embedded channels to drive app installs and partner-referred growth.
Partner with Product and Growth teams to optimize the self-serve buying journey, conversion paths, digital onboarding, and activation funnels.
Develop compelling, merchant-centric messaging, landing pages, digital campaigns, and educational content that articulate the time-saving and compliance benefits of daily automated sales tax.
Plan and execute multi-channel demand generation programs across digital advertising, email nurture streams, partner co-marketing, and industry activations.
Utilize modern marketing technology, automation, and AI-powered tools to scale campaign testing, optimize messaging variations, and eliminate friction across marketing funnels.
Track and analyze full-funnel PLG telemetry and marketing performance metrics (install-to-activation rates, customer acquisition cost, retention, and ROI) to steer marketing investments and campaign optimizations.
AI Proficiency
Use approved AI and automation tools to streamline operations, including project setup, documentation accuracy, sales queue handling, and invoicing workflows.
Build reusable prompts, templates, and lightweight automations to reduce manual rework and help delivery teams prepare client projects faster.
Track efficiency and data quality gains, sharing effective AI workflows and best practices across the team.
What AI success looks like:
Demonstrated experience applying practical AI/automation tools to improve day-to-day workflow speed, quality, and documentation accuracy.
A proactive mindset for identifying process bottlenecks and building scalable, reusable solutions.
What you’ll bring
7+ years of experience leading complex, cross-functional technical programs at a SaaS or enterprise technology organization.
Proven track record delivering programs involving subscription billing, payments/checkout workflows, or complex enterprise platform and integrations.
A track record of driving accountability across a matrixed organization without direct authority.
Experience delivering against fixed milestones and deadlines, including legacy platform migrations.
Executive-level communication skills, with the ability to distill technical and commercial trade-offs into clear recommendations.
Comfort using AI tools in your daily work to synthesize information and move faster.
Preferred
Experience with product-led growth (PLG) or self-serve funnels.
Experience with POS, property-management, or e-commerce partner integrations.
A background in tax, compliance, or fintech.
Solid foundation in Agile, Scrum, or SDLC delivery frameworks
A bachelor’s degree in business, technology, information systems, or a related field, or equivalent experience.
- You’ll bring experience using AI and AI-related technologies, ready to thrive here.
- You’ll apply AI every day to business challenges - improving efficiency, contributing solutions, and driving results for your team, our company, and our customers.
- You’ll grow with AI by staying curious about new trends and best practices, and by sharing what you learn so others can benefit too.
Total Rewards
In addition to a great compensation package, paid time off, and paid parental leave, many Avalara employees are eligible for bonuses.
Health & Wellness
Benefits vary by location but generally include private medical, life, and disability insurance.
Inclusive culture and diversity
Avalara strongly supports diversity, equity, and inclusion, and is committed to integrating them into our business practices and our organizational culture. We also have a total of 8 employee-run resource groups, each with senior leadership and exec sponsorship.
What You Need To Know About Avalara:
We’ve already built an industry-leading cloud compliance platform, processing over 54 billion customer API calls and over 6.6 million tax returns a year. Our growth is real - we're a billion dollar business - and we’re not slowing down until we’ve achieved our mission - to be part of every transaction in the world.
We’re bright, innovative, and disruptive, like the orange we love to wear. It captures our quirky spirit and optimistic mindset. It shows off the culture we’ve designed, that empowers our people to win. We’ve been different from day one. Join us, and your career will be too.
We’re An Equal Opportunity Employer
Avalara is transforming tax compliance into a seamless, automated digital experience. Within our Micro & Emerging Business unit, we are building a unified self-serve compliance platform for small merchants and lodging operators by bringing DAVO and MyLodgeTax together.
As a Senior Program Manager, you will lead the cross-functional operations of this flagship initiative. You will drive alignment, accountability, and execution across dedicated engineering teams, central platform groups, business development, billing systems, and shared services. Reporting to Evan Wright (VP & GM, SMB Business), this role gives you startup-style agility and scope backed by the data, customers, and infrastructure of an established global SaaS leader.
Lead program delivery. Own the integrated plan, milestones, and critical path for the DAVO and MyLodgeTax consolidation, including the platform rebuild, customer migration, and security and compliance deadlines.
Run the cross-team operating model. Set up operating rhythms, dependency maps, and clear service agreements with engineering, central platform, business development, filing operations, and corporate systems teams.
Drive billing and systems work. Coordinate roadmaps and delivery for card and ACH checkout, self-serve pricing and quoting, HubSpot, ERP integrations, and the APIs underneath them.
Align partner integrations. Coordinate timelines across POS and property-management integrations, marketplace apps, and integration partners so customers can sign up and onboard without talking to sales.
Give executives clear visibility. Build dashboards tracking self-serve conversion, support volume, and acquisition economics, and write decision memos that make trade-offs easy to act on.
Modernize how programs run. Use AI tools for status updates, risk detection, and documentation, and help CPMO turn what works here into playbooks for the rest of Avalara.
#LI-Remote
What Your Responsibilities Will Be:
Lead the end-to-end go-to-market strategy, campaign planning, and execution for DAVO to accelerate merchant acquisition, trial sign-ups, and active user growth.
Own marketing initiatives across app marketplaces, POS ecosystems (e.g., Clover, Square, Toast, Shopify, and others), and merchant-embedded channels to drive app installs and partner-referred growth.
Partner with Product and Growth teams to optimize the self-serve buying journey, conversion paths, digital onboarding, and activation funnels.
Develop compelling, merchant-centric messaging, landing pages, digital campaigns, and educational content that articulate the time-saving and compliance benefits of daily automated sales tax.
Plan and execute multi-channel demand generation programs across digital advertising, email nurture streams, partner co-marketing, and industry activations.
Utilize modern marketing technology, automation, and AI-powered tools to scale campaign testing, optimize messaging variations, and eliminate friction across marketing funnels.
Track and analyze full-funnel PLG telemetry and marketing performance metrics (install-to-activation rates, customer acquisition cost, retention, and ROI) to steer marketing investments and campaign optimizations.
AI Proficiency
Use approved AI and automation tools to streamline operations, including project setup, documentation accuracy, sales queue handling, and invoicing workflows.
Build reusable prompts, templates, and lightweight automations to reduce manual rework and help delivery teams prepare client projects faster.
Track efficiency and data quality gains, sharing effective AI workflows and best practices across the team.
What AI success looks like:
Demonstrated experience applying practical AI/automation tools to improve day-to-day workflow speed, quality, and documentation accuracy.
A proactive mindset for identifying process bottlenecks and building scalable, reusable solutions.
What you’ll bring
7+ years of experience leading complex, cross-functional technical programs at a SaaS or enterprise technology organization.
Proven track record delivering programs involving subscription billing, payments/checkout workflows, or complex enterprise platform and integrations.
A track record of driving accountability across a matrixed organization without direct authority.
Experience delivering against fixed milestones and deadlines, including legacy platform migrations.
Executive-level communication skills, with the ability to distill technical and commercial trade-offs into clear recommendations.
Comfort using AI tools in your daily work to synthesize information and move faster.
Preferred
Experience with product-led growth (PLG) or self-serve funnels.
Experience with POS, property-management, or e-commerce partner integrations.
A background in tax, compliance, or fintech.
Solid foundation in Agile, Scrum, or SDLC delivery frameworks
A bachelor’s degree in business, technology, information systems, or a related field, or equivalent experience.
- You’ll bring experience using AI and AI-related technologies, ready to thrive here.
- You’ll apply AI every day to business challenges - improving efficiency, contributing solutions, and driving results for your team, our company, and our customers.
- You’ll grow with AI by staying curious about new trends and best practices, and by sharing what you learn so others can benefit too.
Total Rewards
In addition to a great compensation package, paid time off, and paid parental leave, many Avalara employees are eligible for bonuses.
Health & Wellness
Benefits vary by location but generally include private medical, life, and disability insurance.
Inclusive culture and diversity
Avalara strongly supports diversity, equity, and inclusion, and is committed to integrating them into our business practices and our organizational culture. We also have a total of 8 employee-run resource groups, each with senior leadership and exec sponsorship.
What You Need To Know About Avalara:
We’ve already built an industry-leading cloud compliance platform, processing over 54 billion customer API calls and over 6.6 million tax returns a year. Our growth is real - we're a billion dollar business - and we’re not slowing down until we’ve achieved our mission - to be part of every transaction in the world.
We’re bright, innovative, and disruptive, like the orange we love to wear. It captures our quirky spirit and optimistic mindset. It shows off the culture we’ve designed, that empowers our people to win. We’ve been different from day one. Join us, and your career will be too.
We’re An Equal Opportunity Employer
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Who's Hiring
Top Industries Hiring
- Banking & Financial Services
- Technology & Software
- Aerospace & Defense
- Construction & Real Estate
- Energy
Senior Level Director of Flight Operations Jobs: Frequently Asked Questions
How do I get a senior level director of flight operations job?
Candidates who land these roles typically bring a combination of FAA certification, demonstrated command authority, and a history of leading safety programs or flight departments at scale. Employers at this level look for executives who have managed crews, navigated regulatory audits, and shaped operational standards, not just followed them. A strong record of cross-functional leadership and measurable safety outcomes gives candidates a clear edge.
Which companies hire senior level director of flight operationss?
Companies hiring senior level director of flight operationss right now include Stripe, Amazon, and BNH, based on current listings on Migrate Mate as of November 2026. Hiring at this level tends to come from commercial carriers, regional airlines, cargo operators, corporate flight departments, and aviation services firms that require a senior executive to own the full flight operations function.
Are there remote senior level director of flight operations jobs?
Yes, though most roles in this field involve on-site or operational presence given the nature of flight oversight. About 47% of senior level director of flight operations openings are remote or hybrid as of November 2026, and those positions typically involve corporate aviation planning, regulatory affairs, or multi-base operations management rather than hands-on flight line supervision.
What makes a director of flight operations role senior level?
Senior level director of flight operations roles are defined by enterprise-wide accountability, not just departmental management. These positions own regulatory compliance across the entire flight program, set operational policy, lead and develop aviation leadership teams, and report directly to executive stakeholders. The expectation is that the person in the role shapes how the organization flies, not just that they maintain existing standards.
Which industries hire the most senior level director of flight operationss?
Senior Level director of flight operations roles concentrate in Banking & Financial Services, Technology & Software, and Aerospace & Defense, based on current listings on Migrate Mate as of November 2026. These sectors drive hiring at this level because they operate complex, high-volume, or safety-critical flight programs that require experienced executive leadership to manage regulatory risk, crew performance, and operational continuity at scale.