AI Strategy & Solutions Consultant

Job Description

Position: AI Strategy & Solutions Consultant

Reports To: Chief Operating Officer

Location: Remote

Type: Full-time, exempt

About the Role

Worthwhile is pursuing a consultative service model that repositions the firm from capacity provider to strategic partner. Instead of responding to client requests with proposals to build, we respond with a structured process to determine whether the right thing to build is being built at all. The AI Solutions Consultant is the person who makes this model work — they sell the engagement, lead the strategic analysis, present the recommendation, and plan the execution path if the recommendation is to proceed.

This is not a consulting role grafted onto a services firm. It is the core revenue-generating position in Worthwhile’s next operating model. You are equal parts business developer, strategic thinker, and delivery planner. You will challenge client executives on their assumptions, tell them when they shouldn’t build something, and earn their trust by being right. 

Primary Responsibilities

Revenue Ownership & Pipeline Leadership (approximately 30–40% of time)

• Identify and qualify Pathfinder opportunities within Worthwhile's existing and prospective client base.
• Lead positioning conversations that demonstrate strategic authority and earn the right to a structured decision engagement.
• Own the pipeline from initial conversation through signed engagement letter.
• Collaborate with the COO on pricing strategy and proposal development.
• Build and maintain Worthwhile's credibility narrative using case studies, cost-of-building-wrong data, and retrospective examples from delivery history.
• Contribute to building the Pathfinder playbook, sales materials, and repeatable processes.
• Mentor other team members as the function scales, helping establish a repeatable consulting and sales motion.

Pathfinder Engagement Leadership (approximately 40–50% of time)

• Own the Pathfinder engagement end-to-end, from kickoff through executive presentation.
• Run stakeholder discovery interviews to surface the real problem behind the stated request.
• Translate client initiatives into economic terms: problem value, viable options, and ROI under conservative, expected, and optimistic scenarios.
• Build the options analysis across build, buy, configure, AI-enable, build smaller, and do nothing.
• Develop the risk assessment covering execution, technology, organizational, and market dimensions.
• Author and present the Pathfinder Playback to the client's executive team with a clear go/no-go recommendation and a prioritized roadmap with decision gates.

Delivery Planning (approximately 15–25% of time)

• When the recommendation is to build, translate the strategic decision into a concrete execution plan.
• Define the milestone structure, delivery timeline, and risk mitigation approach.
• Establish decision gates within the build phase that keep execution accountable to the original recommendation.
• Own the handoff to the delivery team, ensuring they inherit a clear scope, prioritized backlog, and measurable success criteria.
• Remain available as a strategic checkpoint during execution to prevent scope drift.

This role requires occasional client travel for discovery sessions and executive presentations.

Qualifications

Required

• Five or more years of professional experience spanning business development, management consulting, or strategic delivery leadership in a technology services or product environment.
• Demonstrated ability to lead executive-level conversations about business outcomes, not just project status.
• Proven ability to drive user adoption and organizational change — you understand that successful technology delivery requires managing people, not just projects, and you know how to bring skeptical stakeholders along.
• Experience leading adoption initiatives such as stakeholder alignment, training strategy, internal communications, or change readiness assessments that determined whether a technology investment actually stuck.
• Experience building financial models, ROI analyses, or business cases that informed significant investment decisions.
• Track record of selling professional services engagements in the $25K–$100K+ range.
• Strong written and verbal communication — the Pathfinder Playback must read like it came from a top-tier consulting firm, delivered by someone who knows what it takes to actually achieve business outcomes.
• Comfort operating with autonomy in a small, distributed team where the playbook is still being written.

Preferred

• Experience in a firm that transitioned from time-and-materials to value-based or fixed-fee pricing.
• Familiarity with software architecture trade-offs and AI/ML feasibility assessment at a conceptual level. 
• Background in digital transformation, product strategy, or technology advisory roles.
• Experience with mid-market clients (companies with $10M–$500M in revenue).
• Familiarity with CRM tools, particularly Salesforce.

What Success Looks Like

In Your First 90 Days

• You have completed your first Pathfinder engagement alongside the COO and internalized the playbook.
• You have taken over pipeline management for active Pathfinder opportunities.
• You understand Worthwhile’s delivery history well enough to draw on it in client conversations.

In Year One

• You have sold and delivered 8–10 Pathfinder engagements.
• At least two clients have expanded into ongoing consulting or build engagements as a result of a Pathfinder recommendation.
• Clients describe Worthwhile as a strategic advisor, not a vendor.
• You have built a pipeline that gives the firm clear visibility into the next quarter’s consulting revenue.
• The COO no longer reviews every deliverable — the playbook is proven and the team trusts it.

About You

You are a highly motivated and results-oriented professional with a proven track record of building and nurturing strategic partnerships. You thrive in a fast-paced environment and have a passion for generating revenue and driving business growth. You have excellent communication and negotiation skills, with the ability to develop and maintain relationships with key stakeholders. You are strategic, and analytical, and have a keen eye for identifying new business opportunities. You are a natural leader who excels at collaborating with cross-functional teams to achieve common goals.

Above all, you align with our core values, demonstrating a passion for problem-solving and an unwavering commitment to innovation and growth. 

About Worthwhile

Worthwhile helps mid-market companies out-innovate their competition through software and data. We utilize a Design Thinking methodology to continuously design, build, and run digital transformation initiatives that deliver real business value in the professional services, finance, and healthcare sectors.

Our culture is unique and defined by our Values in Action. This relentless focus throughout our 25+ year history has enabled us to achieve an unprecedented Net Promoter Score of 98, be listed as an Inc. 5000 Company, and be recognized as one of South Carolina’s Best Places to Work in 2024 (#1), 2023 (#12), 2022 (#4), and 2021 (#2).

At Worthwhile we are a destination for people seeking the most fulfilling work. Our team members are marked by our core values: 

• Advancing Mastery: Our value is ever-increasing because we get better at getting better.
• Enduring Partnerships: We achieve transformative results, cultivating dynamic lasting relationships.
• Constructive Conflict: Caring people with distinctive voices and humble spirits yield exceptional ideas.
• Industrious Joy: Diligent effort, shared purpose – and a little levity – produce meaningful work.