VP, Information Technology

This is not a traditional IT operation. We run no on-premise servers. Our entire infrastructure is cloud-based, and our predominantly remote workforce operates on Macs. Our core collaboration stack includes Google Workspace, Zoom, Slack, and Claude. We are a technology-forward company that expects IT to operate the same way: modern, automated, and continuously improving.

You'll inherit a solid foundation and a capable team of 8. Things work today, but we need to prepare for the next phase. Your job is to bring the executive leadership, process maturity, and strategic vision needed to evolve IT into a world-class function that grows alongside the business.

If you thrive in environments where the problems are complex, the pace is fast, and the stakes are high, this role was built for you.

Define and execute a multi-year IT strategy aligned to company growth objectives, with a focus on scalability, security, and operational excellence.

Serve as a key member of the senior leadership team, advising the CTO and functional leaders on technology investments, risks, and opportunities.

Build and maintain a forward-looking technology roadmap that anticipates business needs and keeps the organization ahead of the curve.

Oversee all enterprise IT infrastructure including cloud environments, networks, endpoints, and SaaS platforms.

Ensure systems availability, performance, and reliability meet or exceed SLAs across the organization.

Lead IT operations including helpdesk, asset management, vendor relationships, and IT service management (ITSM) processes.

Implement and operationalize cybersecurity policies and standards set by the CISO, covering identity and access management, threat detection, incident response, and data protection.

Partner with Legal, Compliance, and the CISO to ensure adherence to SOC 1, SOC 2, and other applicable frameworks.

Champion a culture of security awareness across the organization.

Be an active daily user of AI tools to improve your own productivity and model AI-forward behavior for the organization.

Drive automation of routine IT tasks including ticket triage, provisioning, access management, and reporting, with the goal of eliminating manual overhead wherever possible.

Own AI cost governance including vendor relationship management, usage tracking, quota management, and reporting to budget owners across the organization.

Evaluate emerging technologies and pilot innovative solutions that provide competitive advantage or cost leverage.

Partner with product and engineering teams to align internal tooling with the company's broader technology vision.

Lead, mentor, and grow a high-performing IT team of 8, fostering a culture of ownership, continuous improvement, and collaboration.

Attract and retain top technology talent, building organizational depth across infrastructure, business technology, security operations, and IT operations.

Establish clear goals, performance standards, and career development pathways for all direct and indirect reports.

Own the IT budget, driving cost efficiency without sacrificing quality or reliability.

Manage strategic vendor relationships and negotiate contracts to maximize value and minimize risk.

Report regularly to leadership on IT performance, spend, and strategic progress.

12+ years of progressive IT leadership experience, with at least 2 years in a VP-level or equivalent executive role.

Proven track record leading IT at a SaaS or technology company, ideally through periods of rapid growth or organizational transformation.

Deep hands-on experience with cloud infrastructure (AWS or GCP), enterprise security frameworks, and modern ITSM practices.

Experience owning enterprise business systems (CRM, telephony, ERP) and partnering with business stakeholders on system strategy and optimization.

Experience managing a cloud-native, predominantly remote workforce on Mac endpoints.

Demonstrated ability to build, lead, and inspire cross-functional technology teams.

Strong executive presence with the ability to communicate complex technical concepts clearly to non-technical stakeholders.

Strategic thinker who can balance long-term vision with short-term execution and operational demands.

Experience managing multi-million dollar IT budgets and vendor portfolios.

Fluency across enterprise IT domains including networking, cloud platforms, endpoint management, identity and access management, and cybersecurity.

Hands-on, daily experience with AI tools (e.g., Claude, ChatGPT, Copilot) and a strong point of view on how AI should transform IT operations.

Experience with automation platforms and a track record of applying them to reduce manual IT workload.

Experience with modern telephony and contact center platforms, including AI-native and automation-forward solutions.

Ability to evaluate build vs. buy decisions and architect scalable, cost-effective solutions.

Bullish on AI and automation as a force multiplier for IT teams; sees routine manual work as a problem to be solved, not accepted.

Entrepreneurial and adaptable, comfortable operating in ambiguity and building process maturity where it's needed.

Collaborative and low-ego, with a genuine commitment to serving the business and its people.

Data-driven decision-maker who holds themselves and their team to high standards of accountability.

Passionate about building inclusive, people-first technology organizations.

At Bestow, we’re proud to be awarded for our team members, innovative products, and culture. Our standard benefits include:

Competitive salary and equity based on role

Policies and managers that support work/life balance, like our flexible paid time off and parental leave programs

100% paid-premium option for medical, dental, and vision insurance

Lifestyle stipend to support your physical, emotional, and financial wellbeing

Flexible work-from-home policy and open to remote

Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting

Employee-led diversity, equity, and inclusion initiatives

Recent Employer Awards include:

Best Place for Working Parents 2023 + 2024 + 2025

Great Place to Work Certified, 2022 + 2023 + 2024 + 2025

Built In Best Places to Work, 2022 + 2023 + 2025

Fortune’s Best Workplaces in Texas 2022 + 2023

Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024

We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member.

Thanks for considering a job at Bestow!