Job Title: Senior Director, Engineering - Flickr

Job Level: M5

Location: Remote, within approved U.S. states (see below)

Flickr is one of the most beloved photography platforms in the world, and this role sits at the center of its next chapter. As Senior Director of Engineering, you’ll own the technical strategy and organizational direction for Flickr’s entire engineering function - leading a team while staying genuinely close to the technology, the craft, and the people building it. At Flickr, senior leaders go wide and deep. You’ll be as comfortable in a conversation with the CFO about financial tradeoffs as you are pair programming with an IC3 or debating architecture with an engineer. This is a real seat at the table and a chance to shape how one of the internet’s most iconic platforms evolves.

Compensation: Awesome is committed to fair and equitable compensation practices. The salary range for this role is $175,000-$273,600. This position is also remote-friendly, and as such, compensation will ultimately be in line with the location in which the position is filled. Various factors, such as defined competency leveling and geographic location, will determine the final compensation for this role.

Benefits: Health, dental, vision insurance with 100% premium coverage for you and dependents. Health Savings Account contributions covering 90%+ of annual deductible. 401(k) with company match and immediate vesting. Professional development and learning opportunities. Remote work support (internet, fitness, coworking space reimbursements). Company-sponsored therapy and coaching sessions.

Your Opportunity:

Engineering Strategy and Vision

• Collaborate with the General Manager to shape and refine Flickr’s engineering vision, ensuring alignment with business strategy and product direction.
• Lead the development and execution of engineering initiatives that drive platform reliability, product velocity, and technical excellence.
• Identify and lead high-impact efforts to close technical gaps and capitalize on opportunities that advance Flickr’s competitive position.
• Partner with SmugMug engineering leadership to surface shared opportunities and drive outcomes across the Awesome portfolio.

Technical Leadership

• Stay genuinely close to the technology - engage meaningfully at the code and architecture level, understand the engineering experience, and help shape Flickr’s technical culture.
• Serve as a credible technical voice in executive conversations, translating complex engineering tradeoffs into clear business context.
• Champion engineering craft and a culture of continuous learning, innovation, and ownership across the team.

Team Leadership and Development

• Lead, mentor, and develop a team of engineering managers and building leaders who are accountable, effective, and growing.
• Proactively assess talent, identify skill gaps, and align team development strategies with Flickr’s organizational needs.
• Foster a team environment where engineers are engaged, challenged, and set up to do their best work.

Financial and Operational Ownership

• Oversee full financial management for engineering, including budget setting, expense management, and AWS and cloud infrastructure costs.
• Hold decision-making authority on significant contractual agreements with external vendors and partners.
• Serve as the engineering business owner to Awesome’s Executive Team, influencing and negotiating decisions with lasting business and financial impact.

What You Bring:

• Deep experience leading engineering organizations, with a track record of developing strong leaders.
• Genuine technical depth - you engage meaningfully at the code and architecture level and are as comfortable in the weeds as you are in with the CTO.
• Proven ability to translate business strategy into engineering execution with clear, measurable outcomes.
• Hands-on familiarity with AWS at scale - you understand the infrastructure decisions that drive both product reliability and cost.
• Strong financial acumen - you own budgets, navigate tradeoffs, and make resource decisions with confidence.
• The presence and credibility to operate as a business owner with a C-suite audience — you bring a point of view and earn trust.
• Experience building and scaling engineering teams in consumer-facing, global-scale product environments.
• A thoughtful, objective approach to organizational design - you assess gaps clearly and build for sustained strategic success.

Beyond The Skills:

• This role reports to: General Manager, Flickr
• The systems we use include: Jira, Google Suite, Slack, AWS

What We Offer You:

**Comprehensive Benefits**

- 4-day work week

- Health, dental, vision insurance - 100% premium coverage for employee and dependents

-  HSA contributions covering 90%+ of annual deductible

- 401(k) with company match and immediate vesting

- Unlimited PTO (and we mean it!)

- Learning & development opportunities for personal and professional growth

- Remote work stipends (internet, fitness, coworking space)

- Company-sponsored therapy and coaching sessions

- Flexible spending accounts available

- Company-sponsored phone plan

- A fully remote work environment (+ a coworking space reimbursement if you prefer)

***Applications will be accepted on an ongoing basis up until 8/6/26***

Work Authorization: Candidates must be legally authorized to work in the U.S. Please note that we are unable to provide visa sponsorship for this position.

Location: This is a remote position, and candidates must be physically located in one of the following states: California, Colorado, Florida, Illinois, Maryland, Massachusetts, Michigan, Minnesota, Nevada, New Jersey, New York, North Carolina, Oregon, Texas, Utah, Virginia, and Washington.

All employees must perform work duties from a Company-approved location. Any change to your remote work location, whether temporary or permanent, requires prior approval from your manager and the People Team.

A Little About Us:

Our purpose is simple: building a better world through the power of photography. For over two decades, we have led the photography industry and thrived as a private, mission-focused, values-led company. We are a Certified Evergreen brand. We are also a Certified Great Place to Work, Climate Neutral Certified, and members of the Conservation Alliance.

We’re building iconic brands that connect people through photography and unleash the value of the stories they tell. We make products that thrill photographers of all types, crafting experiences that empower them to preserve their precious memories, share their art, and run their businesses.

A career at Awesome is much more than a job. Our people come first, and we invest in their growth and prioritize their well-being. Your work will contribute to our mission while leaving a positive, lasting impact on our community and our world.

Our expanding family of brands includes SmugMug, Flickr and MODE Events.

AI Use Restrictions:

While we may encourage people to use AI systems during their role to help them work faster and more effectively, please do not use AI assistants during the application and during the interview processes. We want to understand your personal interest in Awesome without mediation through an AI system, and we also want to evaluate your non-AI-assisted skills.*

*This requirement does not apply to those who require the use of AI for necessary accommodations.

EEOC Statement:

Awesome seeks to thrill customers around the world, and building a diverse team is essential to our success. We are committed to providing equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or expression, marital status, veteran status, medical condition, or any other characteristic protected by applicable laws. We encourage diverse candidates to apply and are dedicated to fostering an inclusive and respectful workplace for all. We’re committed to providing equal opportunities and cultivating an inclusive culture. We believe that embracing diversity is integral to innovation and progress.

ADA Requirements:

At Awesome, we strive to create an accessible and inclusive application and selection process. We are committed to providing reasonable accommodations to job applicants with disabilities to facilitate their participation in the recruitment, selection, and assessment processes. Should you require an accommodation, please contact our People Operations Team by email at jobs@smugmug.com, and we will work with you to meet your accessibility needs.

Job Title: Senior Director, Engineering - Flickr

Job Level: M5

Location: Remote, within approved U.S. states (see below)

Flickr is one of the most beloved photography platforms in the world, and this role sits at the center of its next chapter. As Senior Director of Engineering, you’ll own the technical strategy and organizational direction for Flickr’s entire engineering function - leading a team while staying genuinely close to the technology, the craft, and the people building it. At Flickr, senior leaders go wide and deep. You’ll be as comfortable in a conversation with the CFO about financial tradeoffs as you are pair programming with an IC3 or debating architecture with an engineer. This is a real seat at the table and a chance to shape how one of the internet’s most iconic platforms evolves.

Compensation: Awesome is committed to fair and equitable compensation practices. The salary range for this role is $175,000-$273,600. This position is also remote-friendly, and as such, compensation will ultimately be in line with the location in which the position is filled. Various factors, such as defined competency leveling and geographic location, will determine the final compensation for this role.

Benefits: Health, dental, vision insurance with 100% premium coverage for you and dependents. Health Savings Account contributions covering 90%+ of annual deductible. 401(k) with company match and immediate vesting. Professional development and learning opportunities. Remote work support (internet, fitness, coworking space reimbursements). Company-sponsored therapy and coaching sessions.

Your Opportunity:

Engineering Strategy and Vision

• Collaborate with the General Manager to shape and refine Flickr’s engineering vision, ensuring alignment with business strategy and product direction.
• Lead the development and execution of engineering initiatives that drive platform reliability, product velocity, and technical excellence.
• Identify and lead high-impact efforts to close technical gaps and capitalize on opportunities that advance Flickr’s competitive position.
• Partner with SmugMug engineering leadership to surface shared opportunities and drive outcomes across the Awesome portfolio.

Technical Leadership

• Stay genuinely close to the technology - engage meaningfully at the code and architecture level, understand the engineering experience, and help shape Flickr’s technical culture.
• Serve as a credible technical voice in executive conversations, translating complex engineering tradeoffs into clear business context.
• Champion engineering craft and a culture of continuous learning, innovation, and ownership across the team.

Team Leadership and Development

• Lead, mentor, and develop a team of engineering managers and building leaders who are accountable, effective, and growing.
• Proactively assess talent, identify skill gaps, and align team development strategies with Flickr’s organizational needs.
• Foster a team environment where engineers are engaged, challenged, and set up to do their best work.

Financial and Operational Ownership

• Oversee full financial management for engineering, including budget setting, expense management, and AWS and cloud infrastructure costs.
• Hold decision-making authority on significant contractual agreements with external vendors and partners.
• Serve as the engineering business owner to Awesome’s Executive Team, influencing and negotiating decisions with lasting business and financial impact.

What You Bring:

• Deep experience leading engineering organizations, with a track record of developing strong leaders.
• Genuine technical depth - you engage meaningfully at the code and architecture level and are as comfortable in the weeds as you are in with the CTO.
• Proven ability to translate business strategy into engineering execution with clear, measurable outcomes.
• Hands-on familiarity with AWS at scale - you understand the infrastructure decisions that drive both product reliability and cost.
• Strong financial acumen - you own budgets, navigate tradeoffs, and make resource decisions with confidence.
• The presence and credibility to operate as a business owner with a C-suite audience — you bring a point of view and earn trust.
• Experience building and scaling engineering teams in consumer-facing, global-scale product environments.
• A thoughtful, objective approach to organizational design - you assess gaps clearly and build for sustained strategic success.

Beyond The Skills:

• This role reports to: General Manager, Flickr
• The systems we use include: Jira, Google Suite, Slack, AWS

What We Offer You:

**Comprehensive Benefits**

- 4-day work week

- Health, dental, vision insurance - 100% premium coverage for employee and dependents

-  HSA contributions covering 90%+ of annual deductible

- 401(k) with company match and immediate vesting

- Unlimited PTO (and we mean it!)

- Learning & development opportunities for personal and professional growth

- Remote work stipends (internet, fitness, coworking space)

- Company-sponsored therapy and coaching sessions

- Flexible spending accounts available

- Company-sponsored phone plan

- A fully remote work environment (+ a coworking space reimbursement if you prefer)

***Applications will be accepted on an ongoing basis up until 8/6/26***

Work Authorization: Candidates must be legally authorized to work in the U.S. Please note that we are unable to provide visa sponsorship for this position.

Location: This is a remote position, and candidates must be physically located in one of the following states: California, Colorado, Florida, Illinois, Maryland, Massachusetts, Michigan, Minnesota, Nevada, New Jersey, New York, North Carolina, Oregon, Texas, Utah, Virginia, and Washington.

All employees must perform work duties from a Company-approved location. Any change to your remote work location, whether temporary or permanent, requires prior approval from your manager and the People Team.

A Little About Us:

Our purpose is simple: building a better world through the power of photography. For over two decades, we have led the photography industry and thrived as a private, mission-focused, values-led company. We are a Certified Evergreen brand. We are also a Certified Great Place to Work, Climate Neutral Certified, and members of the Conservation Alliance.

We’re building iconic brands that connect people through photography and unleash the value of the stories they tell. We make products that thrill photographers of all types, crafting experiences that empower them to preserve their precious memories, share their art, and run their businesses.

A career at Awesome is much more than a job. Our people come first, and we invest in their growth and prioritize their well-being. Your work will contribute to our mission while leaving a positive, lasting impact on our community and our world.

Our expanding family of brands includes SmugMug, Flickr and MODE Events.

AI Use Restrictions:

While we may encourage people to use AI systems during their role to help them work faster and more effectively, please do not use AI assistants during the application and during the interview processes. We want to understand your personal interest in Awesome without mediation through an AI system, and we also want to evaluate your non-AI-assisted skills.*

*This requirement does not apply to those who require the use of AI for necessary accommodations.

EEOC Statement:

Awesome seeks to thrill customers around the world, and building a diverse team is essential to our success. We are committed to providing equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or expression, marital status, veteran status, medical condition, or any other characteristic protected by applicable laws. We encourage diverse candidates to apply and are dedicated to fostering an inclusive and respectful workplace for all. We’re committed to providing equal opportunities and cultivating an inclusive culture. We believe that embracing diversity is integral to innovation and progress.

ADA Requirements:

At Awesome, we strive to create an accessible and inclusive application and selection process. We are committed to providing reasonable accommodations to job applicants with disabilities to facilitate their participation in the recruitment, selection, and assessment processes. Should you require an accommodation, please contact our People Operations Team by email at jobs@smugmug.com, and we will work with you to meet your accessibility needs.

This role is not open to visa sponsorship or transfer of visa sponsorship including those on H1-B, F-1, OPT, STEM-OPT, or TN visa, nor is it available to work corp-to-corp.

For the Allconnect website click here. Curious how Allconnect fits into Red Ventures? Click here.

Curious how Home fits into Red Ventures? Click here.

You’ll lead the team that builds and scales Red Ventures’ data infrastructure, using Databricks, Spark, and our proprietary platforms to move data across the business and turn raw data into the analytics we run on. As a Director who stays close to the technical details, you’ll set multi-year direction and grow a team of engineers and engineering managers, while making sure your team has the context and guidance to move fast on their own. Our data team exists to make data easy to use for everyone, and this role owns how we get there, in close partnership with the business leaders who depend on that data.

What You’ll Do

• Lead a team of data engineers and engineering managers building large-scale, real-time data pipelines in Spark
• Act as the primary technical liaison to business leadership, translating trade-offs between technology and business priorities in both directions
• Set the multi-year technical direction for Data Engineering and communicate that strategy across both technical and business audiences
• Partner with data scientists, analysts, and business stakeholders to turn business requirements into data products the team builds against
• Represent Data Engineering in cross-functional and executive planning, building alignment across engineering, product, and business leaders
• Set the architectural direction and standards for how data moves across platforms, from streaming ingestion through ETL to aggregation and analytics, hold your managers and teams accountable to that direction, and establish the engineering and agile practices that support delivery speed and quality
• Stay close to the technical details to guide architecture design decisions, performance tuning, and tradeoff calls, and to give your team the context they need to move quickly without waiting on you
• Work with your teams and the RV Data Platform team to design scalable solutions across distributed systems using AWS, Databricks, and modern big data technologies
• Champion a governance-first mindset across your team, making sure the way we collect, move, and use data protects the privacy of the people behind it
• Manage and develop the data engineering managers on your team, setting the bar for how they coach, hire, and run their teams
• Own career development across your org, building growth paths for individual contributors and managers alike, and coaching through regular, direct feedback
• Hold the team accountable for delivering high-quality, scalable solutions across the full data lifecycle

What We’re Looking For

• 8-10 years of data or software engineering experience, including 5+ years managing engineering teams and at least 1 year managing managers
• Track record of communicating technical strategy and tradeoffs clearly to non-technical executives, and building trust quickly with cross-functional peers
• Deep curiosity about the systems and processes that produce our data, with enough understanding of the source to help your team strengthen and troubleshoot pipelines rather than treating data as a black box
• Track record of leading engineering teams in an agile environment, coaching both engineers and managers, and giving teams enough context to operate independently
• Deep hands-on experience building large-scale Spark applications for batch and streaming workloads
• Experience with modern lakehouse platforms (Databricks or similar) in addition to traditional Spark-based pipelines
• Expertise with the Spark RDD and DataFrame/Dataset APIs, with emphasis on DataFrames, for querying and data manipulation
• Experience with Spark Structured Streaming and SparkSQL, including broadcast joins
• Strong programming background in Python and/or Scala, with SQL fluency across large-scale datasets
• Hands-on experience with AWS data services (Kinesis, S3, Lambda, DynamoDB)
• Experience with ANSI SQL relational databases (Oracle, SQL Server, Postgres, MySQL)
• Strong grounding in distributed systems and distributed data processing frameworks

Compensation:

This range reflects total cash compensation, which may include base salary only or base salary plus target bonus, depending on the role. Where eligible, equity may also be offered separately and not included below. Actual compensation varies based on location, experience, and qualifications.

• Total Cash Compensation Range: $190,000 - $240,000 per year

Additionally, the following benefits are provided by Red Ventures, subject to eligibility requirements.

• Health Insurance Coverage (medical, dental, and vision)
• Life Insurance
• Short and Long-Term Disability Insurance
• Flexible Spending Accounts
• Holiday Pay
• 401(k) with match
• Employee Assistance Program
• Paid Parental Bonding Benefit Program
• Flexible Paid Time Off (PTO): We believe time to rest and recharge is essential.  That’s why we offer a generous and flexible PTO policy.  Full-time employees accrue 20 days of PTO for a full calendar year annually, with an increase to 25 days after five years of service.

Who We Are:

Red Ventures is a global portfolio of high-growth companies — spanning several U.S. businesses,a joint venture in the health services industry,and strategic investments in Europe. Their businesses include The Points Guy, Lonely Planet, Bankrate, the Allconnect Platform, RV Home Client Growth, RV Growth & Transformation, Sage Home Loans Corporation, and more. Across the portfolio, Red Ventures businesses deliver seamless digital experiences for consumers, help Fortune 100 clients solve large-scale digital growth challenges, and create world-class experiences and opportunities for employees. Learn more at redventures.com and follow @RedVentures on LinkedIn and Instagram.

At Red Ventures, we believe diverse, inclusive teams are better. To help you better understand our core values and beliefs, we encourage you to watch this brief YouTube video: Our Belief Statements. This will give you insight into the principles that guide our work and our commitment to fostering an inclusive environment.

Red Ventures is an equal opportunity employer that does not discriminate against any employee or applicant because of race, creed, color, religion, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy or any other basis protected by law. Employment at Red Ventures is based solely on a person’s merit and qualifications.

We are committed to providing equal employment opportunities to qualified individuals with disabilities. This includes providing reasonable accommodation where appropriate. Should you require a reasonable accommodation to apply or participate in the job application or interview process, please contact accommodation@redventures.com.

If you are based in California, we encourage you to read this important information for California residents linked here.

#LI-LR1

At Red Ventures, we believe in real human connection. That’s why we do not hire someone through text, social media, or email only. As part of the hiring process, you should expect live conversations with RV teammates before any offer is made. Also, keep an eye on the sender: we only use official @redventures.com email addresses at the portfolio level or business specific email addresses (e.g., @thepointsguy.com), not ones like “redventurescareer.com.” We will never ask candidates to send money, buy equipment, or share financial account info during your journey with us. You can always find our open roles on redventures.com— if you receive a message that seems suspicious, please use redventures.com to verify the opportunity.

For more, the U.S. Federal Trade Commission has published helpful articles to help individuals learn more about protecting themselves from recruiter scams. If you think you’ve been targeted, feel free to report it to your local authorities. Stay safe out there!

Click here for more details regarding the employee privacy policy: https://www.redventures.com/legal/us-emp-privacy-notice

Questions about this Privacy Notice can be directed to employeerights@redventures.com. Alternatively, you may raise any questions or concerns to your manager, HR Business Partner, or through the Privacy Team.

Company Description

Experian is a global data and technology company, powering opportunities for people and businesses around the world. We operate across a range of markets, from financial services to healthcare, automotive, agribusiness, insurance, and many more. Experian invests in people and new advanced technologies to unlock the power of data. We have an amazing team of 25,200 people in 32 countries.

At Experian Automotive, we are transforming how the automotive industry uses data to drive actionable insights. We help you manage risk, better understand your markets, target the right customers at the right time with the right offer - and keep them coming back. We are the only primary source of consumer, credit, vehicle, and digital identity data assets under one roof. From AutoCheck® Vehicle History Reports to market reporting and advanced marketing solutions, we use our unique data and advanced analytics to help the automotive industry make more informed decisions

Job Description

We are seeking a Vice President of Software Engineering to lead software development for Experian Automotive’s marketing and statistical products. This is a senior leadership position, reporting to our Auto CTO, while working closely with other technology leaders to define and execute our software engineering and AI transformation strategy. This role oversees the design, development, delivery, and scalability of products and platforms, ensuring alignment with business goals while fostering a high-performance engineering culture.

The ideal candidate brings strong technical knowledge in modern application development, strong business and financial acumen to balance innovation with business objectives, and a proven track record of leading technology transformation. This leader will champion AI-driven engineering practices and modern software architectures to boost engineering productivity, accelerate product delivery, and create differentiated customer experiences.

Key Responsibilities

Strategic Leadership

• Define and drive the long-term engineering vision, strategy, and roadmap
• Partner with executive leadership (CTO, Product, Sales and Sales Ops Leaders) to align technology initiatives with business objectives
• Evaluate emerging technologies (Generative AI, Agentic AI, LLMs, MCP, automation platforms) and translate them into measurable business value.
• Lead technology transformation, modernization, and innovation efforts

Engineering Execution

• Oversee end-to-end software development lifecycle (SDLC) including architecture, development, testing, release, and operations
• Ensure delivery of high-quality, scalable, secure, and reliable software systems
• Establish and monitor engineering KPIs (velocity, quality, uptime, cost efficiency)
• Establish an AI-first software engineering framework leveraging GenAI-assisted development, intelligent testing, code generation, documentation, and deployment automation to significantly improve developer productivity and software quality

Architecture & Technology

• Drive architectural decisions, platform strategy, and technology standards
• Ensure modern engineering practices (cloud-native, microservices, DevOps, CI/CD, AI integration where relevant)
• Balance build vs. buy decisions and optimize technology investments

Cross-Functional Collaboration

• Work closely with Product Management to deliver customer-centric solutions
• Partner with sales and sales ops team to listen to voice of customer and improve customer satisfaction
• Partner with Security, Infrastructure, Data, and Operations to ensure integrated delivery and governance for responsible AI
• Align with finance and business leaders on budgeting and ROI for investment

Operational Excellence

• Establish governance, processes, and best practices for engineering operations
• Improve engineering productivity, quality, and predictability
• Manage budgets, vendor relationships, and external partners

Organization & Talent

• Build, lead, and scale high-performing engineering teams across multiple disciplines while fostering an AI-first culture emphasizing continuous learning and upskilling
• Recruit, mentor, and retain top engineering talent and while ensuring we have succession plans & leadership pipelines

Qualifications

Experience

• 15+ years of software engineering experience with at least 5+ years in senior leadership roles
• Proven track record of leading distributed engineering teams in US and overseas
• Experience delivering complex, enterprise-scale or high-growth SaaS platforms with high availability, scalability and performance (SLA & RTO)
• Experience developing AI-enabled customer-facing products or integrating AI capabilities into enterprise applications.
• Experience in setting up framework to establish delivery predictability and cycle time improvements
• Knowledgeable about FinOps for cloud cost efficiency and ROI on capital investments

Technical Expertise

• Strong background in modern software architectures (AWS, APIs, MCPs)
• Experience with DevOps, CI/CD pipelines, and agile methodologies
• Understanding of Generative AI, LLMs, AI application architecture, integrating AI services, and responsible AI practices/governance
• Experience in B2B frontend UI, backend microservices and batch job development
• Knowledgeable about REST, Node.js, React, Python, Terraform, AWS RDS

Leadership Skills

• Exceptional strategic thinking and execution capability
• Proven ability to lead large-scale organization transformation focused on change management and adoption of new technologies
• Ability to influence at the executive level through effective presentation skills
• Strong communication and stakeholder management skills

Education

• Bachelor’s or Master’s degree in Computer Science, Engineering, or related field (MBA preferred but optional)

Additional Information

Our uniqueness is that we celebrate yours. Experian’s people first, inclusive and purpose driven culture is multi award-winning; World’s Best Workplaces™ 2025 (Fortune Global Top 25), Great Place To Work™ in 26 countries to name a few. Check out Experian Life on social or explore our Careers Site to understand why.

Our compensation reflects the cost of labor across several U.S. geographic markets. The base pay range for this position is listed above. Within this range, individual pay is determined by work location and additional factors such as job-related skills, experience, and education. This position is also eligible for a variable pay opportunity and a comprehensive benefits package.

Experian is proud to be an Equal Opportunity Employer for all groups protected under applicable federal, state and local law, including protected veterans and individuals with disabilities. If you have a disability or special need that requires accommodation, please let us know at the earliest opportunity.

Benefits/Perks:

• Comprehensive executive level total rewards package
• Flexible time off including unlimited vacation, volunteer time off, and 12 paid holidays
• This a US based, Remote position with periodic travel. #LI-Remote
• Core benefits including medical, dental, vision, and matching 401K
• Explore all our exciting benefits here: https://yourexperianbenefits.com/cand-index.html

Location: Caribbean (Remote) Job Type: Executive | Remote About the Role: Join as a remote Head of Engineering to lead and inspire globally distributed software development teams with an emphasis on innovation, quality, and speed.

VP Engineering, CTO Track (Confidential) | Brydon Group Portfolio Company | Remote US

Every day, pediatric physical, occupational, and speech therapists change children’s lives—but their legacy software makes the job harder than it should be. The Brydon Group, a private equity firm specializing in profitable, recurring-revenue software and services companies, is in the final weeks of acquiring a healthcare SaaS company with passionate customers, strong cash flow, and a mandate to rebuild the tech stack for the next decade. As the first full-time technology executive—hired as VP of Engineering with a clear path to CTO—you’ll lead that transformation end-to-end: modern .NET services, an accessible modern front-end, HIPAA-grade cloud infrastructure, and AI-powered clinical features that free clinicians to focus on kids, not clicks.

A note on confidentiality: this is a pre-close acquisition, so the company name is confidential at this stage. Qualified candidates sign an NDA early in the process and receive full detail on the company, financials, and thesis directly from the CEO and the Brydon deal team.

Opportunity

• Lead the ground-up modernization of a mission-critical EHR and billing platform serving pediatric therapy practices.
• Join at the start of an aggressive growth plan: the goal is to 10x the software business over five years through organic growth and acquisition, backed by committed PE capital.
• Own the multi-year technology vision while remaining hands-on—perfect for a director-level (or rising senior manager) leader ready for the top seat.
• Work directly with a product-led CEO and a seasoned senior designer; inherit two eager engineers who know the codebase cold and are hungry for mentorship.
• Shape engineering culture, hiring roadmap, and best practices from Day 1 in a high-trust, low-bureaucracy environment. No token-tracking, no bureaucracy—unlimited AI tooling, go build.
• Build HIPAA-compliant AI features (ambient documentation, treatment-plan recommendations, smart scheduling) that clinicians will love—and competitors will chase.

What You Will Own

Technology Strategy & Roadmap

• Define and socialize a phased modernization plan aligned to product, clinical, and business goals.
• Advise the CEO and Board on architecture, AI adoption, and cloud investment decisions.

Modernization & New Product Delivery

• Upgrade the legacy .NET platform to modern .NET 8⁄9+ and retire end-of-life dependencies without disrupting active clinical workflows.
• Replace embedded legacy UI with a WCAG 2.1 AA-compliant modern front-end (React, Vue, or Angular)—and write some of that code yourself.
• Launch companion mobile apps (leading the work, not necessarily building it) that improve clinician usability and patient workflow efficiency.
• Decompose services over time and move toward multi-tenant architecture as scale demands.

Security & Compliance

• Own HIPAA Security Rule posture and drive SOC 2 Type II readiness, executing a security roadmap with third-party audit support.
• Bring security intuition to product and design decisions—MFA, encryption, secure-by-default patterns.

Data & AI

• Ship clinician-facing AI features by integrating best-in-class models and vendors—applied AI, not custom model development.
• Champion AI-assisted development across the engineering organization while meeting privacy, safety, and compliance standards.
• Lay the foundation for a data and analytics platform as the business scales.

Team Leadership & External Representation

• Mentor and grow the existing engineers into a high-performing team; recruit as the roadmap demands.
• Be a full-time, present leader for a team that’s ready for one.
• Represent technology with customers, partners, auditors, and the Board.

What Makes You a Strong Fit

• 8+ years of software engineering experience, including 4+ years leading teams as Director, Sr. Manager, or equivalent.
• Hands-on expertise in the Microsoft .NET ecosystem—you can be productive with this team in the short term.
• Comfortable personally writing modern front-end code (React, Vue, or Angular), with an appreciation for consumer-grade UX.
• A real tech-debt story: you’ve taken something janky, figured out what to keep and what to upgrade, built it into a roadmap, and delivered it at a pace the business could absorb.
• Experience in healthcare IT, digital health, or EHR/EMR software; familiarity with HIPAA-regulated environments.
• Experience shipping applied-AI product features (LLM/vendor integration) and using AI tools in daily development.
• Player/coach leadership style: expect roughly 50% hands-on coding in year one, shifting toward leadership as the team grows.
• Business fluency: budgets, metrics, and communicating decisions to executives and the Board.

Nice to Have

• Pediatric therapy, EHR/EMR, or revenue-cycle/billing software experience.
• Full legacy-modernization or re-platforming leadership.
• Cloud/DevOps depth (Azure preferred)—an MSP handles infrastructure today, so this is not a Day 1 burden.
• SOC 2 Type II audit ownership, ambient clinical NLP, or PE-backed scale-up experience.

Location & Travel

• Remote within the United States. The anchor acquisition is in the southeastern US.
• Expect significant travel to the Southeast US hub during the first 6–12 months, ~20% travel thereafter.

Compensation: $225–275K OTE; Potential for Equity.

Apply now and get a response within 24 hours

VP Engineering, CTO Track | Pediatric Therapy SaaS | Remote USEvery day, pediatric physical, occupational, and speech therapists change children’s lives—but their legacy software makes the job harder than it should be.

VP Engineering, CTO Track (Confidential) | Brydon Group Portfolio Company | Remote US

Every day, pediatric physical, occupational, and speech therapists change children’s lives—but their legacy software makes the job harder than it should be. The Brydon Group, a private equity firm specializing in profitable, recurring-revenue software and services companies, is in the final weeks of acquiring a healthcare SaaS company with passionate customers, strong cash flow, and a mandate to rebuild the tech stack for the next decade. As the first full-time technology executive—hired as VP of Engineering with a clear path to CTO—you’ll lead that transformation end-to-end: modern .NET services, an accessible modern front-end, HIPAA-grade cloud infrastructure, and AI-powered clinical features that free clinicians to focus on kids, not clicks.

A note on confidentiality: this is a pre-close acquisition, so the company name is confidential at this stage. Qualified candidates sign an NDA early in the process and receive full detail on the company, financials, and thesis directly from the CEO and the Brydon deal team.

Opportunity

• Lead the ground-up modernization of a mission-critical EHR and billing platform serving pediatric therapy practices.
• Join at the start of an aggressive growth plan: the goal is to 10x the software business over five years through organic growth and acquisition, backed by committed PE capital.
• Own the multi-year technology vision while remaining hands-on—perfect for a director-level (or rising senior manager) leader ready for the top seat.
• Work directly with a product-led CEO and a seasoned senior designer; inherit two eager engineers who know the codebase cold and are hungry for mentorship.
• Shape engineering culture, hiring roadmap, and best practices from Day 1 in a high-trust, low-bureaucracy environment. No token-tracking, no bureaucracy—unlimited AI tooling, go build.
• Build HIPAA-compliant AI features (ambient documentation, treatment-plan recommendations, smart scheduling) that clinicians will love—and competitors will chase.

What You Will Own

Technology Strategy & Roadmap

• Define and socialize a phased modernization plan aligned to product, clinical, and business goals.
• Advise the CEO and Board on architecture, AI adoption, and cloud investment decisions.

Modernization & New Product Delivery

• Upgrade the legacy .NET platform to modern .NET 8⁄9+ and retire end-of-life dependencies without disrupting active clinical workflows.
• Replace embedded legacy UI with a WCAG 2.1 AA-compliant modern front-end (React, Vue, or Angular)—and write some of that code yourself.
• Launch companion mobile apps (leading the work, not necessarily building it) that improve clinician usability and patient workflow efficiency.
• Decompose services over time and move toward multi-tenant architecture as scale demands.

Security & Compliance

• Own HIPAA Security Rule posture and drive SOC 2 Type II readiness, executing a security roadmap with third-party audit support.
• Bring security intuition to product and design decisions—MFA, encryption, secure-by-default patterns.

Data & AI

• Ship clinician-facing AI features by integrating best-in-class models and vendors—applied AI, not custom model development.
• Champion AI-assisted development across the engineering organization while meeting privacy, safety, and compliance standards.
• Lay the foundation for a data and analytics platform as the business scales.

Team Leadership & External Representation

• Mentor and grow the existing engineers into a high-performing team; recruit as the roadmap demands.
• Be a full-time, present leader for a team that’s ready for one.
• Represent technology with customers, partners, auditors, and the Board.

What Makes You a Strong Fit

• 8+ years of software engineering experience, including 4+ years leading teams as Director, Sr. Manager, or equivalent.
• Hands-on expertise in the Microsoft .NET ecosystem—you can be productive with this team in the short term.
• Comfortable personally writing modern front-end code (React, Vue, or Angular), with an appreciation for consumer-grade UX.
• A real tech-debt story: you’ve taken something janky, figured out what to keep and what to upgrade, built it into a roadmap, and delivered it at a pace the business could absorb.
• Experience in healthcare IT, digital health, or EHR/EMR software; familiarity with HIPAA-regulated environments.
• Experience shipping applied-AI product features (LLM/vendor integration) and using AI tools in daily development.
• Player/coach leadership style: expect roughly 50% hands-on coding in year one, shifting toward leadership as the team grows.
• Business fluency: budgets, metrics, and communicating decisions to executives and the Board.

Nice to Have

• Pediatric therapy, EHR/EMR, or revenue-cycle/billing software experience.
• Full legacy-modernization or re-platforming leadership.
• Cloud/DevOps depth (Azure preferred)—an MSP handles infrastructure today, so this is not a Day 1 burden.
• SOC 2 Type II audit ownership, ambient clinical NLP, or PE-backed scale-up experience.

Location & Travel

• Remote within the United States. The anchor acquisition is in the southeastern US.
• Expect significant travel to the Southeast US hub during the first 6–12 months, ~20% travel thereafter.

Compensation: $225–275K OTE; Potential for Equity.

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