Director Technology Strategy Jobs in Portland, ME

Strategy Development & Thought Partnership - 20%

• Partner with the SVP to develop and sharpen the strategy for the organization-bringing analysis, market and customer perspective, and well-formed options to inform the SVP's decisions.
• Pressure-test the SVP's thinking and surface the questions, tradeoffs, and risks that lead to better decisions; act as a sounding board on the hardest problems.
• Frame complex, ambiguous problems into clear choices and recommendations, helping shape where the organization should focus and why.

Strategic Execution & Accountability - 20%

• Translate the strategy and priorities into clear operating plans with defined goals, milestones, owners, and success metrics.
• Track commitments end to end, drive follow-through, and hold teams and leaders accountable for progress against priorities, escalating to the SVP when needed.
• Bring structure, focus, and momentum to complex, high-ambiguity initiatives so they stay on track and get finished.

Operating Rhythm & Cadence - 15%

• Build and run the operating rhythm for the organization-leadership meetings, business reviews, escalation forums, and cross-functional check-ins-that keep teams aligned and accountable.
• Prepare the SVP and leadership team for key meetings: agendas, pre-reads, decisions needed, and clear follow-ups, so time is spent well and nothing falls through the cracks.
• Prepare and synthesize materials for SLT/ELT and Board reviews on the SVP's behalf, turning complex performance and strategy into clear, decision-ready narratives.
• Standardize operating processes and expectations across teams to drive consistency and efficiency.

Performance Visibility & Insight - 15%

• Build and maintain the reporting and dashboards that give the SVP and leadership team timely visibility into delivery, implementation health, value realization, customer satisfaction (NPS, retention trends), and operational performance.
• Turn data into insight and recommendation, not just reporting-flag gaps, risks, and where attention is needed so issues surface early enough to act on.
• Standardize metric definitions and reporting across teams so performance is measured consistently.

Cross-Functional Program Leadership - 15%

• Lead high-priority, cross-functional initiatives on the SVP's behalf, managing timelines, risks, dependencies, and outcomes through to delivery.
• Remove barriers, coordinate the right people, and streamline decision-making to keep initiatives moving.
• Serve as a trusted, dependable point of coordination across all functions of the business - e.g. Sales, Account Mgmt / Growth, CRV, Product, Tech, Finance, Marketing, Legal, HR.

Operating Model & Economics Support - 10%

• Partner with the SVP to develop the customer value operating model-helping shape how functions should connect, where handoffs and accountabilities need to be clearer, and bringing forward options for how the model should evolve.
• Work with Finance, Rev Ops, and CRV leadership to build the data and analysis behind the organization's economics, keeping external revenue, cost allocation, ARR influence, and value attribution distinct rather than commingled.
• Prepare the analysis, materials, and options that inform the SVP's decisions on the model, investment tradeoffs, and priorities.

Continuous Improvement & Ways of Working - 5%

• Identify and implement better ways of working that improve how the organization operates, leveraging tools, automation, and practical AI solutions.
• Incorporate lessons learned, data, and customer feedback into operational adjustments, building a habit of continuous improvement.

Required Qualifications

• Significant experience in strategic operations, chief-of-staff, strategy, or program leadership in a high-growth or complex matrixed environment, at a scope consistent with a Director / Sr. Director level.
• A strong track record both of helping shape strategy-bringing analysis, options, and judgment to senior decisions-and of making it run, turning priorities into plans, operating rhythms, and tracked commitments that deliver measurable outcomes.
• Both a strong strategic thinker and a strong executor: senior enough to be a true operating partner who sharpens the strategy, and hands-on enough to drive execution and follow-through.
• Strong analytical and problem-framing skills, with the ability to take ambiguous problems and turn them into clear choices, options, and recommendations.
• Proven ability to partner across functions and business areas to coordinate initiatives and drive accountability without owning those functions directly.
• Strong executive presence: confident and respected, able to build trust across the leadership team, influence without authority, and hold peers and teams accountable on the SVP's behalf.
• Strong communication skills, with the ability to simplify complexity, maintain clarity, and align teams and senior leaders around a shared plan.
• A reputation for being collaborative, organized, analytical, proactive, and highly dependable-bringing structure to ambiguity and momentum to fast-paced environments.

Required Qualifications

• Experience in Professional Services, implementation/onboarding, customer success, or value-realization functions.
• Familiarity with the economics of services work-revenue, cost allocation, ARR influence, and value attribution-and comfort partnering closely with Finance and Rev Ops.
• Deep customer-centricity, with experience using customer insight (NPS, retention drivers) to shape strategy and operational improvements.
• Experience building dashboards and performance frameworks and using data to inform decisions.
• Experience implementing process improvements, operating cadences, and continuous-improvement frameworks.
• Experience applying automation and practical AI to improve how teams operate.