Director, Digital Strategy

12 Jul, 2021


Director, Digital Strategy

Portland, OR


Olive’s AI workforce is built to fix our broken healthcare system by addressing healthcare’s most burdensome issues — delivering hospitals, health systems and payers increased revenue, reduced costs and increased capacity. People feel lost in the system today and healthcare employees are essentially working in the dark due to outdated technology that creates a lack of shared knowledge and siloed data. Olive is designed to drive connections, shining a new light on the broken healthcare processes that stand between providers delivering patient care and payers. She uses AI to reveal life-changing outcomes that make healthcare more efficient, affordable and effective. Olive’s mission is to unleash a trillion dollars by connecting a disconnected healthcare system. Olive is improving healthcare operations today, so everyone can benefit from a healthier industry tomorrow.

Job Overview:

Olive is seeking a seasoned, strategic digital leader to drive our digital strategy to the next level. Reporting to the Vice President of Marketing, this role will lead the effort to optimize the overall user experience for our digital site(s) while engaging our customers across all audiences.

This leader will develop short-term and long-range strategic plans for our website, while managing our agency partners, who are an extension of the overall team. This role will directly manage all site content and site operations. They will work closely with other teams including paid media, product marketing, program management, content, creative, research, analytics, communications and brand.

Essential Duties and Responsibilities:

  • Develop and implement the digital strategy and roadmap for the Olive digital experience to drive unique, sustainable and engaging content with our customers through a differentiated and compelling end-to-end experience.
  • Establish brand differentiation and sustain success through continuous analysis of market trends, competitive influences, and performance of digital properties.
  • Collaborate with the full marketing team and other teams to deliver high-quality digital experiences across the customer lifecycle (awareness, consideration, conversion, engagement, retention).
  • Develop user flows to align marketing off-site tactics with a seamless, intuitive, and brand-building on-site experience. Leverage qualitative and quantitative data to prioritize work for the agency partners, as well as internal creative and product teams, assessing risk and tradeoffs.
  • Drive innovation for Olive through researching new methods of online storytelling.
  • Provide leadership to the digital team; building capabilities and supporting them in their development while nurturing a collaborative and dynamic culture.
  • Experience using data and metrics to back up assumptions and assertions of business value. Ability to develop a nuanced understanding of our products and customers, that will lead to creating effective strategies.
  • Demonstrated ability to make high quality/high impact decisions in the absence of data and figure out how to gather data (through experiments, tests, etc.) to support your decisions. Comfort with ambiguity is key.
  • Demonstrated ability to innovate, build, launch, and lifecycle-manage successful products that customers love.
  • Superb communication and influencing; aptitude to influence cross-functional teams without formal authority; proven ability to lead and motivate across multiple disciplines in order to accomplish a common goal.
  • Establish strong, mutually beneficial relationships with teams outside of marketing.
  • Attention to detail executing complex projects with cross-functional dependencies; ability to prioritize and focus while effectively managing multiple and shifting priorities in a fast-paced environment.


  • Bachelor’s degree or equivalent professional experience
  • 6+ years of experience in digital strategy, with a focus on user experience and digital storytelling
  • Experience with Google Analytics (or similar measurement platform)
  • Experience managing agency partners (and being a good client)
  • Excellent communication skills (written and verbal)
  • Experience hiring and managing high-performing teams in a fast-paced environment
  • High level of enthusiasm for the website, for Olive and for changing healthcare
  • Test and learn mentality, ability to pivot quickly
  • Startup and/or digital agency experience preferred but not required

At Olive, we’re committed to growing and empowering an inclusive community within our company and industry. This is why we hire and cultivate diverse teams of the best and brightest from all backgrounds, experiences, and perspectives across our organization. Research shows that oftentimes women and other minority groups only apply to open roles if they meet 100% of the listed criteria. Olive encourages everyone — including women, people of color, individuals with disabilities and those in the LGBTQIA+ community — to apply for our available positions, even if they don’t necessarily check every box on the job description.


This job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee. Duties, responsibilities and activities may change or new ones may be assigned.

This job description does not constitute a contract of employment and Olive AI, Inc. may exercise its employment-at-will rights at any time.

Learn more here

Job posted: 2021-07-12