Principal Web Solutions Strategist

About the company

The company is a digital agency full of smart, curious learners who love solving complex problems for higher education organizations. We partner with colleges and universities to navigate digital complexity so their marketing drives measurable impact for their brand and enrollment goals.

We bring deep expertise and a consultative mindset to everything we do—asking the right questions, challenging assumptions when needed, and always centering around our clients’ goals. In this role, you’ll be the subject-matter expert who frames the solution as part of the win-strategy for higher-ed web solutions engagements, helping prospective clients understand where they’re stuck and advising them on the right path forward, not just pitching a product.

We’re building toward a future where the company is higher education’s most trusted advisory and implementation partner, and this role sits on the front lines of that journey—translating institutional challenges into smart, actionable web strategies.

About the Position

At its core, this role exists to win business: owning win-strategy, shaping the story the company tells, engaging directly with clients, and leading pitches and proposals for Web Solutions deals.

The Principal Web Solutions Strategist sits on the company’s Web Solutions Strategy team and plays a critical role at the intersection of business development, strategy, and delivery, in close partnership with the Director of Strategy. This role leads the strategic definition of Web Solutions deals, from early conversations with prospective clients through high-level involvement during delivery—ensuring that what the company sells is thoughtful, viable, and aligned with how we deliver value.

In the sales process, the Principal Web Solutions Strategist crafts and communicates the vision and then defines the solution. You will own the majority of strategic airtime in client conversations:

• Properly diagnosing client pain points and goals

• Leading pitches and proposal strategy

• Creating proposals and pitch materials, bringing in subject-matter experts and delivery leads when specialized input is needed or the opportunity requires a custom deliverable

• Presenting audits and strategic recommendations

• Clearly explaining the company’s approach and the “how” behind our work

Proposal and pitch work is core to this role. It’s strategic work, not just production work. You’ll set the direction and narrative, developing customized proposals and pitch materials that communicate a persuasive, tailored solution that meets the client’s needs while effectively communicating the value the company would bring to the engagement.

You’ll work closely with the company’s Sales and Web Solutions teams, collecting collaborative input and feedback as you build the final proposal or pitch for delivery.

Through deep expertise in higher education websites and digital ecosystems, you’ll build trust quickly and confidently answer complex technical and strategic questions, partnering with the company subject matter experts as needed.

After a project is won, you’ll stay engaged at key moments to ensure the project direction stays aligned with the vision established during the sales process. You’ll support a strong transition into delivery, participate in select milestones where your context is most valuable, and be available to help flag major strategic misalignments or risks so the team can address them early. This role provides continuity and confidence for the client at pivotal points while empowering the delivery team to lead day-to-day strategy and execution.

Beyond individual projects, you’ll help shape the evolution of the company’s Web Solutions practice. You’ll gather market insights, identify buyer patterns, and partner with our Web Solutions leadership team to shape, inform and refine our offerings and how we talk about the value we bring to potential partners.    i You’ll also contribute to the company’s thought leadership so that the company continues to be seen as a trusted strategic partner for higher education institutions.

Requirements

• 7-10+ years of experience in digital strategy, web strategy, consulting, or agency environments.

• Experience leading or owning delivery of digital projects in an agency and/or higher-education environment, with a solid understanding of how digital disciplines—UX, content strategy, design, and development—fit together and depend on one another. Higher-education experience is strongly preferred; candidates from other complex, highly regulated industries (e.g., healthcare, government, financial services) with comparable client and compliance dynamics are also encouraged to apply.

• Deep expertise in content-intensive website strategy, including UX, content strategy, CMS platforms, accessibility, governance, SEO, and project delivery approaches.

• Executive-level presence and strategic storytelling ability, with demonstrated comfort leading high-stakes pitches, setting vision, building trust with senior stakeholders, confidently owning the room, and influencing business development outcomes. This does not require a formal sales title or a traditional sales background.

• Experience shaping, evolving, or stewarding service offerings or productized solutions.

• Ability to balance pre-sale strategy leadership with high-level delivery involvement without becoming execution-focused.

• Comfortable navigating ambiguity and collaborating across sales, strategy, and delivery teams.

• Strong judgment and decision-making skills, particularly around scope, approach, and strategic tradeoffs.

• An intuitive problem-solver who can rapidly synthesize complex information, identify core problems, and pivot to strategic solutions with speed and precision.

• Natural ability to rally teams, build momentum around a vision, and push deals or initiatives across the finish line.

• Depth of technological understanding across diverse digital ecosystems, ensuring the ability to confidently advise on complex technical solutions and integrations.

• Established or emerging thought leadership and external credibility—for example, conference speaking, published articles or perspective pieces, or a strong professional presence (e.g., LinkedIn) within the higher-ed or digital strategy community.

What Success Looks Like in 6–12 Months

Within 6–12 months, a successful Principal Web Solutions Strategist will:

• Shape web opportunities so that by the time they’re late-stage, everyone is clear on the problem we’re solving, how success will be measured, and the recommended approach.

• Develop and lead proposals and pitches that win, with measurable improvement in the company's win rate on Web Solutions opportunities and wins increasingly driven by the strength of the strategy and story—not just price or scope.

• Sell work that delivery teams describe as “right-sized and well framed,” with minimal need for major re-scoping once projects kick off.

• Lead sales conversations that prospective clients and senior stakeholders regularly describe as advisory, clarifying, and confidence-building (for example, through direct feedback, NPS, or post-pitch debriefs).

• Help evolve our Web Solutions offering by spotting patterns across deals and delivery and turning them into sharper packages, positioning, and case studies.

• Become the person BDRs, BDMs, and Web Solutions Directors naturally pull into complex or ambiguous opportunities when they need help framing the problem and path forward.

• Contribute to visible thought leadership in higher-ed web strategy (talks, webinars, articles, etc.) that we can point to as influencing new or stronger client relationships.

The company Benefits

The company offers a comprehensive medical, dental, and vision insurance package, along with company-paid life insurance as well as short/long-term disability coverage. Benefits also include a 401(k) match up to 4% of pay, paid vacation and sick time, ten holidays including a Flex Day, Summer Fridays, and more!

Each year, the team aims to come together in person for our Annual Summit at a beautiful destination, and throughout the year, leadership shares regular company updates and fosters an open-door culture. We also sprinkle in a healthy dose of fun with team events, friendly competitions, and other surprises that keep things fresh and connected.

Additional Information

Candidates should be comfortable traveling nationally 2-4 times a year for company and/or client meetings.

Candidates must be legally authorized to work in the United States in order to be considered. The company is an e-Verify employer, ensuring compliance with federal employment eligibility requirements.

The company is an Equal Opportunity Employer committed to a diverse workforce, and does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, veteran status, disability, or any other legally protected characteristic.