Scaled Agile, Inc., (SAI) is a global training and enablement platform equipping enterprises with the capabilities needed to compete in an era defined by rapid change, digital complexity, and AI-driven work. Through SAFe®—the world’s most trusted system for enterprise agility—and a growing portfolio of enterprise AI education and enablement programs, we help organizations make better decisions, accelerate value delivery, and build adaptable, high-performing teams.
Supported by a global partner network of more than 400 companies and a vibrant community of more than 2 million trained professionals, SAI equips leaders and teams with the skills, mental models, and operating systems they need to accelerate transformation, improve flow, and unlock value with confidence. Our newest AI-focused offerings are expanding quickly as leaders seek structured, pragmatic guidance on how to become AI-Native and realize ROI where most AI initiatives stall.
SAI is headquartered in Boulder, Colorado. There is no requirement that this person live in Colorado, as we have a virtual team with regular in-person meetings. SAI is a Pledge 1% corporate philanthropy movement member. Through this program, SAI contributes to the local community and seeks to inspire and encourage other companies to do the same.
Job Description:This role is built for sellers who know how to change customer thinking and move deals forward—not wait for perfect alignment or hide behind process.
As an Account Executive, you’ll own the full sales cycle for enterprise and upper-mid-market customers, closing transformation deals typically ranging from $50,000 to $200,000 annually, with clear expansion paths over time.
You’ll sell Scaled Agile’s enterprise solutions by challenging how customers approach Agile, AI adoption, Lean Portfolio Management, and organizational change—helping leaders move from stalled intent to decisive action.
This is a high-autonomy role for someone who thrives in messy buying environments, where urgency must be created, value must be quantified, and decisions rarely arrive fully formed.
What You’ll Do
Lead insight-driven sales conversations - Teach customers something new about the risks of the status quo and the opportunity cost of delaying enterprise change.
Create momentum in mid-sized enterprise deals - Drive opportunities forward when buyers are uncertain, divided, or overloaded—keeping deals moving without over engineering them.
Navigate real buying groups - Engage directors, VPs, and executives across technology, product, finance, and transformation roles—aligning stakeholders without waiting for consensus.
Own the full deal lifecycle - Prospect, qualify, advance, negotiate, and close $50K–$200K opportunities with discipline and urgency.
Build business cases that resonate - Translate Agile and AI transformation into economic, operational, and leadership outcomes that buyers care about.
Collaborate across teams - Work closely with marketing, partners, and delivery to ensure deals close cleanly and customers launch successfully.
Expand accounts intentionally - Land with a focused solution and identify logical expansion paths across training, consulting, and enterprise offerings.
Represent Scaled Agile externally - Engage in industry events and conversations where credibility and point of view matter more than product demos.
What Sets You Up for Success
2+ years of quota-carrying experience in B2B sales, ideally in technology, services, or transformation-focused offerings
Proven success closing $50K–$200K deals with multiple stakeholders
Comfort leading conversations with directors, VPs, and executive sponsors
Strong discovery and qualification skills—you know when a deal is real
Ability to create urgency without being pushy
Experience collaborating with partners or internal specialists to advance deals
Consistent record of meeting or exceeding targets
Familiarity with Agile, AI, or organizational change concepts (you don’t need to be an expert—you need to be credible)
About You
You’re confident, curious, and comfortable challenging customer assumptions
You know rapport is earned through insight, not likability
You simplify complexity and help buyers make decisions
You adapt your message naturally to different audiences
You take ownership of your pipeline, your deals, and your outcomes
You care deeply about customer results, not just closing the deal
Where you’ll be working: We proudly support a collaborative remote environment for our globally distributed teammates, while also using our Boulder office as a resource. #LI-Remote
Compensation: Scaled Agile is committed to fair and equitable compensation practices. The annual on-target compensation range for this role is $120,000 to $210,000, including base salary and any related variable compensation. Final compensation for this role will be determined by various factors such as a candidate's relevant work experience, skills, industry knowledge, certifications, and location.
Wondering if you should apply?
As a company that helps organizations embrace and turn change into opportunity, we’re looking for teammates with diverse experiences who thrive on applying their knowledge in new ways. You don’t need to meet every listed qualification to apply. If you’re motivated by an iterative approach to growth, learning, collaboration, and relentless improvement, we want to hear from you.
Work Differently. Build the Future.