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Director of Sales & Growth – AI & Cloud (Microsoft Practice, Midwest / Central U.S.)

Tailored Management Services Inc Bellevue, WA (Onsite) Full-Time



Director of Sales & Growth – AI & Cloud (Microsoft Practice, Midwest / Central U.S.)

Preferred Locations: Kansas City, MO • Dallas, TX • Des Moines, IA • Chicago, IL
Travel: ~40% (monthly or ad hoc)




Role Overview

The Director of Sales & Growth – AI & Cloud is a senior sales leader responsible for driving revenue growth across Microsoft Azure, Microsoft Fabric, Data, Analytics, and AI solutions. This role focuses on helping enterprise customers modernize their technology stacks through cloud transformation, advanced analytics, and AI adoption.

You will own the full sales lifecycle—from prospecting and qualification through pursuit and close—while building trusted relationships with executive stakeholders and Microsoft field teams. This is a high-impact role for a proven hunter and strategic quarterback who thrives in complex, consultative sales environments.




Key Responsibilities

  • Drive significant revenue growth across Microsoft Azure, Microsoft Fabric, Data & Analytics, Cloud, and AI services.

  • Build and execute joint go-to-market strategies with Microsoft field teams and ecosystem partners such as Databricks and Snowflake.

  • Develop and manage a strong U.S. sales pipeline, including new logo acquisition and expansion within existing accounts.

  • Lead complex enterprise sales cycles, including global/offshore delivery models and large program-based engagements.

  • Champion advanced offerings such as Agentic AI, Generative AI, Microsoft Fabric migrations, document intelligence, and enterprise modernization initiatives.

  • Guide customers in adopting Azure OpenAI, Microsoft 365 Copilot, Power Platform, and emerging AI capabilities.

  • Serve as a trusted advisor to executive stakeholders, aligning technology investments to measurable business outcomes.

  • Consistently achieve or exceed revenue, growth, and customer acquisition targets across assigned territories.

  • Develop detailed account strategies, opportunity plans, and pursuit strategies.

  • Navigate complex client organizations to identify and influence senior and mid-level decision-makers.

  • Collaborate cross-functionally with pre-sales, marketing, and delivery teams across multiple time zones.

  • Build long-term, trust-based client relationships that drive sustained value and repeat business.

  • Act as a leader within the Microsoft partner ecosystem, supporting joint sales motions and strategic alliances.




Qualifications

  • 10+ years of enterprise services sales experience within consulting or IT services organizations.

  • Deep expertise in Microsoft Azure, Data, AI, Cloud enablement, migrations, and modernization initiatives.

  • Bachelor’s degree required.

  • Proven success selling global/offshore delivery models and complex consulting engagements.

  • Demonstrated success in services sales, partner-led joint sales, and Microsoft ecosystem selling.

  • Strong ability to diagnose client challenges and craft solution- and value-based sales strategies.

  • Consistent track record of exceeding sales targets.

  • Experience thriving in fast-paced, high-growth environments.

  • Executive-level relationship management experience, including C-suite engagement.

  • Excellent communication, presentation, negotiation, and stakeholder management skills.

  • High-energy, decisive, and comfortable operating in demanding client environments.

  • Familiarity with CLM, ERP, or Procurement solutions is a plus.




Compensation

Annual On-Target Earnings (OTE): $240K – $320K

  • Base Salary: $120K – $160K

  • Variable Compensation (Uncapped): $120K – $160K

Compensation is based on experience, skills, and location and may vary accordingly.




Benefits & Perks

  • Comprehensive medical, dental, and vision coverage

  • Flexible Spending Accounts (FSA) and Health Savings Accounts (HSA)

  • 401(k) retirement plan

  • Short- and long-term disability and life insurance

  • Employee Assistance Program

  • 120 hours of PTO annually (10 hours/month)

  • 12 paid company holidays, plus a paid July 4th week shutdown

  • Paid sick leave and domestic violence leave per local regulations

  • 5 paid volunteer days annually

  • Career development and growth opportunities

  • Flexible work hours supporting work/life balance

  • Fast-paced, inclusive culture that values innovation and impact




Equal Opportunity Statement

The company is an Equal Employment Opportunity employer and complies with all applicable federal, state, and local nondiscrimination laws. All applicant information will be handled confidentially and in accordance with EEO guidelines.

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Job Snapshot

Employee Type

Full-Time

Location

Bellevue, WA (Onsite)

Job Type

Other

Experience

Not Specified

Date Posted

01/15/2026

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