Director, Strategic Services

Workboard; Chicago (IL); On-site; USD 150,000 - 175,000; Full time

Benefits offered by this job

Flexible PTO

Paid holidays

Health insurance

Employer 401K match

Quarterly bonuses

All-hands meetings

Job summary

WorkBoard is seeking a Director of Strategic Services for WorkBoardAI to guide strategic initiatives with senior executives. You will shape how customers formulate objectives, operationalize plans, and measure impact using data-driven operating models.

The role emphasizes strategic advisory, portfolio alignment, and driving tangible business outcomes across large enterprises. You will partner with Success, Sales, and Product teams to accelerate growth, influence executive decisions, and ensure

Qualifications

• Minimum 10+ years of work experience in strategy, consulting, or related roles.
• Experience leading enterprise-level engagements in SaaS or strategy execution domains.
• Ability to connect business value to technology and influence senior leaders.

Responsibilities

• Lead executive conversations and workshops with C-Level leaders.
• Coach client teams to define, communicate, and operationalize strategic objectives.
• Drive value realization through ROI-based value journeys and renewals.

Skills

Executive stakeholder management

Strategy development

SaaS experience

Tools

Salesforce (SFDC)

Job description

Director, Strategic Services – WorkBoardAI

About WorkBoard

WorkBoard is the pioneer in AI-driven strategy execution solutions, empowering enterprises to align, measure, and achieve their most important outcomes. With our platform, organizations can operationalize strategy in real time, foster alignment across teams, and accelerate growth. Our customers include some of the world’s most innovative companies across technology, financial services, healthcare, and more. We’re backed by top-tier investors and led by a diverse, mission-driven team that’s passionate about redefining how organizations execute strategy at scale. At WorkBoard, you’ll have the opportunity to join a fast-growing, category-defining company where your work directly impacts how leaders shape the future.

The Opportunity

The direct WorkBoard buyer is typically the CEO or GM of a business unit, and our platform is deployed to all employees under the P&L owner – giving the company an exceptionally large market opportunity. As the Director of Strategic Services, this role presents a rare opportunity to see first-hand and influence how companies and teams formulate their strategic objectives, operationalize them to drive results, and make a tangible impact on employee engagement and business outcomes. You will form strategic advisor relationships with C-Level Executives, and coach their teams to define, communicate, and operationalize their results achievement. You will play a pivotal role in making strategic priorities relevant and meaningful at every level of the organization, and being a trusted advisor from pre to post sales. Your results expertise will enable our customers to increase the business results they realize from the WorkBoard platform over time.

The Role

As the Director of Strategic Services, you will provide prospective and new customers with expert advice on how to better execute strategy and maximize performance, drive an excellent platform launch and introduction process and serve as an active guide in the early stages of a customer's journey to define and achieve measurable value that increases over time. You will serve as a trusted advisor to senior leaders and their teams, aligning execution with long-range and short-range goals through scalable, data-driven operating models and high-impact enablement.

What we're looking for:

• You are business-savvy and draw on your combination of real-world experience and education to work seamlessly and fluently with leaders across a wide range of functional disciplines at large enterprises.
• You are a self-starter with strong ownership skills, willing to support many customer accounts, deploying impactful strategies to accelerate our clients’ and WorkBoard’s growth.
• You have a strong interest and experience in strategy development, strategy deployment, and operating model optimization.
• A minimum of 10 years of work experience and ideally, experience at a strategy firm such as McKinsey, Bain, BCG, or a management consulting firm like PwC, Accenture, Deloitte, or Slalom.
• A plus if you have worked for a high-growth B2B SaaS company.
• You have experience in both strategy execution and strategic portfolio management.
• You have an arsenal of successful tactics for connecting business value to technology. You are genuine, warm, positive, engaging, and empathetic.
• Proven experience leading enterprise-level implementation or consulting engagements, ideally in SaaS or strategy execution domains.
• Exceptional communication and storytelling skills; ability to influence at all levels of an organization.
• Passion for helping organizations achieve their best possible results.

You’ll be skilled and super effective at:

• Leading executive conversations and working sessions.
• Deck creation, design, and graphical representation of complex concepts for executive-level presentations.
• Leveraging your natural curiosity to quickly understand a client’s business while demonstrating tact and poise under pressure.
• Delivering exceptional customer experience and value to customers, demonstrated by successfully closing contract renewals and partnering with sales to identify and close expansion and new business opportunities.
• Communicating & listening with the ability to credibly and confidently engage executives.
• Understanding complex, matrix organizations and navigating them effectively to create value for both our clients and the company.
• Mapping and understanding existing strategy execution and portfolio management processes and partner with clients on a path forward.
• Engaging various techniques to deepen customer value over time.

WITHIN ONE MONTH, YOU'LL:

• Build a deep understanding of our buyer, their pain points, our methodology and how we work as a team.
• Deep-dive with Customer Success, Sales, and Product Management teams to learn more about our solution, go-to-market and roadmap and the partnership with the Services team.
• Meet with 5 enthusiastic WorkBoard customers and 5 prospective customers to understand senior leadership challenges and how we help.
• Know your client teams and the objectives and key results they are looking to achieve in the quarter and the next year.
• Be a daily user of WorkBoard and SFDC to help drive rocket ship growth.
• Dazzle a WorkBoard expert with your enthusiastic demo.
• Confidently articulate the value, benefits and relevance of our powerful solution easily and effectively.
• Have action plans in place to achieve the Key Results for your business.

WITHIN THREE MONTHS, YOU'LL:

• Guide 15+ clients in setting and aligning an ROI based value journey.
• Be a valued partner by helping more than 40 leaders use WorkBoard’s Agents, Scorecards, Biz Reviews and Meetings in order to run their business for results, on a weekly basis.
• Spend a great deal of time with our amazing customers both in person and virtually.
• Lead white glove enablement sessions with 20 senior leaders.
• Have successfully secured 2 commitments to be a customer reference.
• Successfully partner with Customer Success to close renewals and identify 3 opportunities for expansion revenue.

WITHIN SIX MONTHS, YOU'LL:

• Have two dozen executive and chief of staff customer relationships that you can tap for insights, references, case studies and thought partnership any time to express the business value WorkBoard is helping them drive for their company.
• Know your customers are continually getting value by creating a successful track-record of closing renewals, securing expansion and up-sell opportunities, and closing services revenue.

THE TEAM

You will be joining a matrixed team focused on igniting and delivering value quickly to our buyers. We are in growth mode, and we are a passionate no-ego bunch that "falls in love" with our customers and is fully dedicated to ensuring their success.

OUR VALUES - WE LIVE BY THE 4 H’S

Humble experts ~ Hungry for the opportunity ~ Intellectually honest~ Operating as one happy team

A FEW OF OUR AWESOME BENEFITS

• Flexible PTO & sick days
• Paid holidays
• Health insurance
• 401K with employer matching
• Quarterly Bonuses based on company performance
• Bi-weekly All-Hands Meetings
• And much more!

The US salary range for this full-time position is $150-175k OTE annual salary. Our salary ranges are determined by role, level and geographic location. Within the range, individual pay is determined by additional factors, including job-related skills, experience, and relevant education or training.