Anna Dickerson-Homan

Program Manager, Web Marketing & AI Enablement at Gusto | Championing AI adoption across marketing orgs

United States

About

I develop AI-enabled GTM systems that optimize marketing performance and bring content to market faster. At Gusto, my focus is on practical AI adoption, automation, and content intelligence that speeds up pipeline and improves team efficiency. I help bring Gusto’s mission to life by making our website clear, accessible, and fast to market so SMBs can spend less time on paperwork and more time growing. I'm a program manager who sees AI tools as a force multiplier for marketing teams. I integrate them into workflows: automating Notion and Gumloop processes, building landing pages and dashboards in Cursor, streamlining stakeholder comms, pulling insights from Slack and internal data using Claude and OpenAI, and helping colleagues go from AI-curious to AI-capable. Before Gusto, I led demand generation in SaaS, cybersecurity, and health tech. What energizes me most is turning complexity into clarity, aligning teams, and building scalable systems that free leaders to focus on growth. I grew up in a small business family, where I learned that the right systems give people their time back. That perspective shapes the grit, empathy, and bias for action I bring to every role. If you’re scaling with purpose and need someone who bridges strategy with execution, let’s connect.

Experience

  • Gusto (2 yrs 4 mos)
    • Senior Program Manager
      May 2025 - Present · 1 yr 2 mos

      As Senior Web Marketing Program Manager at Gusto, I help bring Gusto’s mission to life, ensuring our website is clear, accessible, and fast to market so small and mid-sized businesses can spend less time on paperwork and more time growing. In this role, I: •Lead high-impact web initiatives, including landing page optimizations that doubled performance •Build scalable systems and workflows that help teams move with clarity and speed •Champion accessibility, ensuring our web experience serves all users and meets WCAG standards •Drive AI adoption across marketing workflows to improve efficiency and speed to market •Collaborate closely with product, design, and engineering to align web strategy with business goals I’m grateful to work alongside some of the sharpest, kindest people I know, all deeply committed to helping small businesses thrive.

    • Web Marketing Program Manager
      Mar 2024 - Jul 2025 · 1 yr 5 mos

      Gusto is the top payroll and HR provider for SMBs and start-ups globally. Ranked #1 for G2's 2025 Small Business Payroll, Gusto aims to delight and support small businesses. We serve more than 400,000 businesses with payroll and HR services. Each year we process tens of billions of dollars of payroll and provide employee benefits through one refreshingly easy, integrated platform.

  • Project Manager / Digital Marketing Manager at Critical Insight
    Mar 2021 - Dec 2023 · 2 yrs 10 mos

    Critical Insight is focused on securing America’s most vital organizations and critical infrastructure against cyberattacks through a revolutionary Cybersecurity-as-a-Service model. Industry targets include Healthcare, Rural and Critical Access Hospitals, Aerospace, Cities and Counties, Water Districts, Education, and Manufacturing. As a Project Manager and Digital Marketing Manager, I lead the Marketing initiative to bring cold inbound leads to SAL$. I also: •Led impactful multi-channel marketing programs to drive pipeline and revenue growth at all customer lifecycle stages. •Successfully oversaw the transition of the company website and rebranding to a new CMS (Craft) from Pardot. •Collaborated closely with the sales and customer success team to target and prioritize key accounts. •Developed and executed tailored campaign playbooks, messaging, and integrated marketing campaigns for high-value and high-sensitivity accounts. •Worked with cross-functional teams to launch projects such as the Healthcare Data Breach Report, leveraging DHHS-reported security breaches. •Aligned marketing efforts with sales for effective pipeline acceleration and synchronized messaging. •Managed the creation of case studies and promotional material by working directly with high-value customers. •Analyzed and reported campaign effectiveness to internal teams using Power BI and weekly status check-ins. •Stayed updated on the latest threats, current events, and breaches for enhanced targeting and personalization. •Managed a daily email sharing the latest news with prospects and customers. This email, "The Daily Cybersecurity Blast" is read by thousands every day with an average 47% open rate.

  • Senior Marketing Specialist at Strata Decision Technology
    Oct 2020 - Mar 2021 · 6 mos

    EPSi.io was acquired by Strata Decision Technology (Roper Technologies) in October 2020 for $360 Million. As the leading Healthcare financial performance platform (ranked #1 in KLAS for 15+ years), Strata helps bend the cost curve and make healthcare more affordable to consumers. Strata has a customer base that includes over 400 of the nation's top healthcare delivery systems and is considered the "Gold Standard" in financial planning, analytics, and performance. In my role as Senior Marketing Specialist, I: •Focused on EPSi customer retention following acquisition by Strata Decision Technologies. •Emphasized strong communication and data-driven integrated campaigns. •Handled and prioritized incoming business requests related to sponsorship activation and branding. •Conducted market research to identify customer trends, competitive offerings, and demographic data. •Collaborated with internal teams to understand business objectives and develop, recommend, and implement marketing strategies. •Owned the implementation and execution of marketing campaigns to deepen relationships with existing customers.

  • Senior Marketing Campaign and Operations Manager at EPSi.io
    Feb 2019 - Oct 2020 · 1 yr 9 mos

    Previously owned by Allscripts, EPSi was the industry leader in integrated financial decision support, budgeting, and planning solutions for the healthcare industry. More than 900 hospitals in the U.S., including nine of the top 10 rated hospitals, 128 IDN systems, and 40 global academic facilities relied on EPSi for data-driven insight into managing costs and improving their long-range financial performance. It was sold to Strata Decision Technology in 2020. In my role as Senior Marketing Campaign and Operations Specialist, I: •I formulated and executed a broad, integrated marketing strategy while driving demand to accelerate growth in a highly competitive market. •Directly managed a $1.3MM annual marketing budget while managing a team of 7 contractors and maximizing ROI. •Managed an aggressive campaign providing the first free COVID-19 dashboard to monitor the growth of the pandemic for healthcare executives in collaboration with The Johns Hopkins Hospital to 533 healthcare organizations across the nation. •Launched a successful webinar series, "Voices from the Frontlines," interviewing healthcare finance executives from the top healthcare systems which generated 1k views in 24 hours on our first episode.

  • Director of Marketing at The Agent School
    Sep 2017 - Dec 2018 · 1 yr 4 mos

    The Agent School was a marketing firm started at Market Center #1 in Austin, TX for KW Market Centers all around the US. As the Director of Marketing, I was in charge of: •Launching an online course called RAMP UP, a training course designed for Keller Williams Realty Team Leaders to quickly boost the real estate careers of their agents and improve agent retention for their market centers. •Working closely with executive leadership and top performers at Keller Williams Realty MC #1 to formulate the long-range brand marketing strategy with nearer-term plans, goals, growth objectives, and agreed-upon success measures. •Leading the implementation of the marketing strategy to support market share growth, constantly improve brand engagement by franchisees and agents, and drive intent among home buyers and sellers. •Managing external agency relationships and improve the value of these relationships as well as media planning and spending. •Reporting on key results and other predetermined KPIs regularly. •Developing and manage marketing strategies, standards, and workflows.