Director, Professional Services Engagements

Crisp

About The Position

Crisp is building a world-class Professional Services organization to accelerate customer time-to-value, deepen executive relationships, and drive durable platform adoption. The Engagement Manager (EM) is a critical role within this organization, responsible for leading customer engagements from initial scoping through value realization. This role is best described as a strategic program leader rather than a traditional project manager. Engagement Managers orchestrate multi-workstream delivery across Crisp teams and partners, ensure tight alignment between customer outcomes and Crisp’s commercial goals, and act as the connective tissue between Services, Product, Sales, and Customer Success. Engagement Managers operate in a forward-deployed model, embedding deeply with customers to solve high-impact operational problems using Crisp’s platform. They are accountable not just for delivery quality, but for adoption, expansion, margin, and executive trust.

Requirements

8–12+ years of experience in professional services, consulting, customer delivery, or program leadership roles.
Experience managing complex, multi-workstream enterprise engagements with executive stakeholders.
Background in enterprise SaaS, data platforms, analytics, or AI-enabled solutions strongly preferred.
Demonstrated ability to balance customer outcomes with commercial discipline (margin, scope control, utilization).
Experience working in or alongside forward-deployed, engineering-led, or embedded delivery models.
Strong cross-functional leadership skills with the ability to influence without direct authority.
Comfortable operating in ambiguous, early-stage environments and building structure where none exists.

Nice To Haves

Experience in Retail and/or CPG is a plus.

Responsibilities

Own end-to-end delivery of Professional Services engagements including: Strategy & Innovation Workshops Rapid Value Pilots / Bootcamps Platform Implementations Forward-Deployed Engagements and Dedicated Capacity Pods
Establish and manage engagement governance: scope, milestones, risks, dependencies, and decision forums.
Lead executive-facing status updates and steering committees, ensuring clarity on progress, outcomes, and value delivered.
Manage scope change, tradeoffs, and expectations to protect delivery quality, margin, and customer trust.
Translate customer business objectives into structured delivery plans with clear workstreams, success metrics, and value hypotheses.
Coordinate cross-functional teams spanning: Professional Services delivery resources Product and Engineering Solutions, Sales, and Customer Success Third-party implementation or consulting partners
Drive alignment across stakeholders while maintaining accountability for outcomes.
Partner with Sales and Customer Success on engagement scoping, SOW development, pricing, and resourcing strategies.
Own engagement economics including margin, utilization, and partner costs.
Ensure services engagements accelerate: Sales velocity (shorter deal cycles, larger deal sizes) Product adoption and expansion Net Dollar Retention (NDR)
Identify expansion opportunities and transition points from Services-led value to recurring software revenue.
Plan and manage staffing across Crisp employees and delivery partners.
Forecast demand and resource needs across concurrent engagements.
Ensure optimal use of forward-deployed talent while maintaining delivery quality and team sustainability.
Lead day-to-day execution of partner-delivered or hybrid engagements.
Ensure partners adhere to Crisp delivery standards, methodologies, and reporting expectations.
Act as the single point of accountability for customer outcomes regardless of delivery model.
Define and track value realization metrics for each engagement (time-to-value, adoption, operational impact).
Ensure insights from customer deployments are fed back into Product and Engineering to inform roadmap priorities and product hardening.
Help evolve Crisp’s delivery playbooks, methodologies, and service offerings based on field learnings.