Full-Time

Deployment Strategist

Ground Force Operations

Sitreps

Sitreps

11-50 employees

Veteran career platform and recruiting partner

Compensation Overview

$120k - $145k/yr

+ Bonus (15-30%) + Equity

No H1B Sponsorship

Arlington, VA, USA

In Person

Up to 75% travel; based in Arlington, Virginia.

US Top Secret Clearance Required

Bachelor's

Category
Data & Analytics (1)

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Requirements
  • Bachelor's degree or equivalent professional experience.
  • U.S. military experience in the Army, Air Force, or Marine Corps, with exposure to logistics, sustainment, operational planning, force management, headquarters staff, or other mission planning and execution roles.
  • Strong customer-facing skills with the ability to build trusted relationships and influence stakeholders.
  • Excellent verbal, written, and presentation skills, with the ability to communicate effectively across technical and non-technical audiences.
  • Demonstrated ability to solve complex, ambiguous problems and operate effectively in fast-paced environments.
  • Highly organized with the ability to manage multiple priorities and customer engagements.
  • Passion for supporting U.S. national security and helping customers achieve mission outcomes.
  • Willingness to travel up to 75% in support of customer missions.
Responsibilities
  • Become a trusted advisor to government customers by developing a deep understanding of their organizations, missions, priorities, and operational challenges.
  • Lead customer onboarding, implementation planning, and successful deployment of our platform across government organizations.
  • Drive customer adoption through training sessions, executive briefings, workshops, and ongoing engagement.
  • Partner closely with customer leadership to identify opportunities where our platform can improve decision-making and mission effectiveness.
  • Gather customer feedback and operational insights to influence future product development and roadmap priorities.
  • Coordinate with Product, Engineering, and Customer Success teams to ensure customer needs are effectively communicated and addressed.
  • Develop customer success plans that measure adoption, engagement, and mission outcomes.
  • Create user documentation, implementation guides, training materials, and executive-ready presentations.
  • Present operational insights and platform capabilities to senior military officers, civilian government leaders, and executive stakeholders.
  • Support customer renewals, expansion opportunities, and strategic account growth through exceptional customer engagement.
  • Represent the voice of the customer internally while serving as an ambassador for our platform externally.
  • Support product demonstrations during strategic sales engagements.
  • Facilitate customer workshops focused on operational planning, force readiness, sustainment, and modernization initiatives.
  • Assist with customer pilots, proof-of-concepts, and new capability rollouts.
  • Contribute to thought leadership around defense modernization and operational transformation.
Desired Qualifications
  • Experience as a logistics, sustainment, transportation, operations, or planning officer, or equivalent enlisted leadership experience.
  • High-performing military officers from any Army, Air Force, or Marine Corps branch with demonstrated leadership in operational or strategic assignments are encouraged to apply.
  • Experience supporting Department of Defense customers in Customer Success, Solutions Consulting, Professional Services, Program Management, Implementation, or Forward Deployed roles.
  • Familiarity with Joint Operations, logistics, force planning, defense acquisition, PPBE, sustainment, or modernization initiatives.
  • Experience working with enterprise software, SaaS platforms, data analytics, AI-enabled products, or decision-support tools.
  • Experience briefing senior military leaders, SES civilians, or executive stakeholders.
  • Current U.S. security clearance, or the ability to obtain one with company sponsorship.
  • Experience working in a high-growth startup or entrepreneurial environment.
  • Demonstrated ability to translate customer feedback into product improvements and operational recommendations.

Sitreps helps military veterans transition to civilian careers by providing free, high-quality career resources such as resume guides, networking events, and webinars, building a large veteran community. The platform monetizes by serving as a recruiting partner for employers seeking veteran talent, focusing on private equity, SMBs, and defense technology. It differentiates itself through a veteran-centric approach, founder Kyle Ely’s military background, and programs like the Warrior Class Summit, veteran startup pitch, and an upcoming AI-powered resume builder. Its goal is to scale veteran career success by equipping veterans with resources and connecting them with employers while creating recurring revenue through partnerships and value-added programs.

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

N/A

Founded

2019

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Simplify Jobs

Simplify's Take

What believers are saying

  • Sitreps reported 150+ veterans placed and $180K average compensation by July 2026.
  • Wyatt Frasier’s January 2026 post announced an AI resume builder, pitch contest, and fellowship.
  • Monthly events across Los Angeles, Nashville, New York, Miami, and DC expand deal flow.

What critics are saying

  • Sitreps depends on Kyle Ely’s personal brand; audience fatigue breaks lead flow quickly.
  • Palantir and Chamberlain partnerships remain nonexclusive; stronger veteran recruiters can displace Sitreps.
  • Manual, service-heavy recruiting gives LinkedIn and niche agencies room to copy Sitreps fast.

What makes Sitreps unique

  • Sitreps blends free veteran content with recruiting, creating a two-sided community moat.
  • Kyle Ely and Wyatt Frasier target PE, SMB, and defense tech veterans specifically.
  • Sitreps added webinars, meetups, Chamberlain Fellowship, and Palantir partnership in 2026.

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Benefits

Company Equity

Stock Options

Performance Bonus