Director of Delivery Management

Information Technology Remote USA, United States


Position at Windward Consulting

Windward Consulting is at the forefront of Service-Centric IT. With strategic consulting, unparalleled technical expertise and our proven Windward Service-Centric IT RoadMap, we help our clients align the core competencies of process, organization, information and technology to run the most sensitive and mission-critical IT environments in the world.

If you are looking for an opportunity to be involved with a team of individuals who are working within one of our cutting edge clients solving complex technical challenges then we are looking for you. We are looking for people who are passionate about technology and have a "roll up their sleeves mentality." Here at Windward we offer numerous opportunities to expand your experience in various areas depending upon your aptitude and interests. Our employees are not only passionate and driven, but strive to ensure customer quality is delivered consistently and effective.

The Director of Delivery Management position is responsible for overseeing the delivery portfolio of all projects and staffing engagements within Windward against financial operational targets.  The Director shall directly manage a staff of service delivery managers, project manager, and staffing managers who will manage delivery of a portfolio of projects, while the Director may also directly manage a small portfolio.  The Director and his team shall partner with sales account executives on customer success, extensions & new opportunities, and pull in practice managers for scoping.   This position develops and manages repeatable and best-practice project management methodology.  The delivery management team will also work closely with the practice management on staffing and quality, as delivery consultants and engineers shall be assigned by practices who will hire, contract, and develop staff. 


Required Skills:

  • Minimum of 10 or more years of industry experience within consulting, professional services, or software implementation track record.
  • Minimum of 5 year of experience selling consulting services for IT operations or service management technologies or services.
  • Project Management Professional (PMP) with experience establishing and leading project management offices (PMO) and understanding of PM best practices.
  • Ability to design and implement PMO across a full portfolio of staffing (3mo-1yr+), and small (<$50k) to large ($1M+) projects that fits and balances both customer success and profitability targets.
  • Understanding of PM principles and frameworks that are adopted by large enterprises, such as Scaled Agile Framework (SAFe) Lean-Agile, to appropriately integrate Windward projects into client’s environment.
  • Experience and demonstrated success in account management, account growth and new client acquisition.
  • Proven leadership ability with strong client relationship and consulting skills.
  • Proven professional with long, established track record in project management and service delivery, structuring and completing milestone-based assignments on time and ensuring work on client projects is performed consistently at high quality, and reflects client goals and expectations.
  • Ability to independently provide strategic vision, yet equally experienced with requirements definition, practical solution design, business cases development and solution implementation for clients.
  • Demonstrated ability to collaborate effectively across a consulting organization with other practice Directors/VPs, as well as the Service Delivery personnel.
  • Proven track record of multi-tasking business development, client-side delivery, and people and team management skills.
  • Strong professional and personal integrity with very high ethical standards.



  • Bachelor’s degree; Advanced Business or Computer Technology Degree a plus


Desired Background:

  • Excellent business development skills with experience in business-to-business technology sales.
  • Possesses the qualities and characteristics that support development of junior team members to grow a thriving services practice.

Essential Duties & Responsibilities:

  • 60% Delivery Management: Supervise program and project execution across multiple accounts and teams ensuring compliance with standards and methodology. Review statements of work to ensure they describe client objectives and provide clear and achievable objectives and milestones. Drive coordination across consulting teams to ensure alignment of resources, and to manage, escalate and mitigate project and account risks as they are encountered. Escalate and collaborate with practice management on quality assurance across staffing, requirements analysis, solution architecture and design, development and integration tasks, testing processes and documentation, along with overarching delivery execution.
  • 20% Sales Support: Collaborate with account executives and practice management on a sales pipeline by developing, nurturing, and maintaining existing clients, and identifying extension, expansion and new opportunities.  Share knowledge and insight on client needs, environment and solutions  to supporting development of client proposals, presentations and business case materials.
  • 20% Practice and Staff Development: Development of portfolio and project management best practice and standards to be applied to an appropriate degree across all levels of customer engagements. Participate in service delivery and project management personnel recruitment and provide direct involvement in personnel reviews and retention programs to fuel sustainable business growth and high-quality service execution.


  • Travel is based upon specific program and client requirements and will thus fluctuate based on current workload and sales activity. Must be open to working remotely at an out-of-town client site for an extended period of time on special occasions.


Windward strives to attract and retain the best individuals and provide an environment where they can all grow professionally and build a rewarding career. We continually strive to create an environment that balances work life and offers benefits that will enhance the compensation package. We offer Medical, Dental, Vision, Flexible Spending Accounts, Short Term Disability, Long Term Disability, Life Insurance and AD&D, as well as the option to purchase additional Life Insurance and AD&D, Paid Time Off, Personal Leave, Holidays, 401(k) plan with company match and work/life balance.

Windward Consulting is proud to be an Equal Opportunity Employer. Applicants are considered for all positions without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, ancestry, marital or veteran status.

WINDWARD CONSULTING GROUP, INC. (WINDWARD) PROVIDES EQUAL EMPLOYMENT OPPORTUNITY WITHOUT REGARD TO AN APPLICANT’S COLOR, RACE, SEX, PREGNANCY, NATIONAL ORIGIN, AGE, DISABILITY, RELIGION, MARITAL STATUS, GENETIC INFORMATION, VETERAN STATUS, OR ANY OTHER CHARACTERISTICS PROTECTED BY FEDERAL, STATE OR LOCAL LAW. WE WILL CONSIDER THIS APPLICATION ACTIVE FOR 90 DAYS AFTER OUR RECEIPT. THEREAFTER, YOU MUST REAPPLY IF FURTHER INTERESTED IN EMPLOYMENT. I CERTIFY THAT ALL ANSWERS GIVEN BY ME ARE TRUE, ACCURATE AND COMPLETE, I UNDERSTAND THAT THE FALSIFICATION, MISREPRESENTATION OR OMISSION OF ANY FACT ON THIS APPLICATION (OR ANY OTHER ACCOMPANYING OR REQUIRED DOCUMENTS) OR PROVIDED ORALLY, WILL BE CAUSE FOR DENIAL OF EMPLOYMENT OR IMMEDIATE TERMINATION OF EMPLOYMENT, REGARDLESS OF WHEN OR HOW DISCOVERED. The application will be given every consideration, but its receipt does not imply that the applicant will be employed. In exchange for the Company’s considering my application for employment, I authorize investigation of all statements contained in this application and any supporting documents. I authorize Windward to secure information about my experience from former employers, educational institutions, government agencies, or any references I have provided, and for those parties to provide information concerning my experience, and I hereby release all parties from any liability arising from such investigation. In exchange for the Company’s considering my application for employment, I hereby authorize my former employer to release to Windward any personnel information and records, favorable or otherwise, which my employer has kept regarding my employment, including my work performance. I understand that Windward may retain photocopies of my records for its files, whether I am offered employment or not. I hereby release all parties, including my former employer and Windward from any liability arising from the release, review and retention of any records pertaining to me.