Software Acceleration Associate - Washington, DC

About the job At Keystone AI , we are a team that lives by teamwork. However, it’s not the work that drives us, it’s the respect, trust, and care for each other that defines us as a team. We’re a diverse community of trendsetters who do our best work in a fun, relaxed environment. Technology never stops evolving and neither do we. We’re always looking for the best and brightest team players to join us. About the Position Are you an ambitious outbound seller with 1–2 years of experience and a passion for software sales? Ready to accelerate your career into full cycle account management and close deals—not just source them for other sales reps who share your commission? This 6 month Software Sales Acceleration Program is designed to fast track high potential talent into our Software Account Management (SAM) organization. This is a temporary program role with full benefits and a clear outcome at the end of six months: Top performers will advance directly into a Software Account Representative (SAR) role Exceptional performers may be considered for Sr Software Account Representative (Sr SAR) placement Those who do not meet performance expectations may conclude participation at the end of the program If you want a true pathway into Software Account Management, you will want to take a close look at this role. Responsibilities In this role, you’ll work in a high energy, outbound sales environment built to strengthen your SaaS selling foundation while preparing you for full cycle responsibilities. You will: Own outbound prospecting, targeted outreach, and pipeline generation Qualify opportunities and create momentum for SAM sales cycles Deliver compelling messaging to SMB and mid-market prospects Execute structured call, email, and LinkedIn cadences Collaborate with SAM leaders and sales partners to refine conversion strategies Strengthen your SaaS sales acumen through ongoing coaching, training, and immersion in our platform Demonstrate performance and consistency across a structured evaluation framework You’ll get exposure to real selling, not just booking meetings—setting you up for success as you transition into the SAM family. Who We’re Looking For Associate's degree or equivalent experience, required 1 to 2 years of outbound sales experience, required. 2+ years of related experience, preferred. Confidence communicating with decision makers via phone, email, and social Ability to manage volume, objection handling, and pipeline creation Desire to learn full cycle sales and move into a closing role Comfort with structured goals, metrics, and performance accountability A growth mindset and coachability Willingness and ability to meet clients face-to-face as you grow your network and unleash sales success. Must be 18 years of age or older. Must successfully complete pre-employment screening process, as required. Must successfully complete any required training or orientation courses, as needed. What’s in It for You This role is intentionally designed as a launchpad into Software Account Management, offering: A 6‑month accelerated program focused on outbound software selling Competitive compensation package with performance-based incentives Hands‑on exposure to our SAM teams and full sales cycle Real opportunity to move into SAR or Sr SAR based on performance following 6-months’ performance Skill‑building that positions you for long‑term career growth in software sales This isn’t just another outbound role—it’s a career advancement program. Program Outcomes At the end of the 6‑month program: High performers → Software Account Representative (SAR) Exceptional performers → Sr SAR Non‑performers → Program completion without transition This creates a fair, performance‑based path and allows you to take ownership of your growth which doesn’t end with the Sr SAR role: SAM Family Software Account Representative “SAR” Sr Software Account Representative “Sr SAR” Software Account Executive “SAE” Sr Software Account Executive “Sr SAE” Key Software Account Executive “Key SAE” What We Offer Life requires balance. So we provide benefits around health and wellness, continued education, and work/life balance to help you live your best life when you’re working…and when you’re not. Medical, dental, and vision plans, plus a wellness program with added incentives 401(k) savings plan with company match and employee stock purchase plan Continuing education benefits with tuition assistance programs Paid time off including holidays, vacation, sick, personal, and year-end close Who We Are At Keystone AI , we’re a team fiercely devoted to the success of local businesses. We’ve been around for over 100 years, always with one goal in mind — helping small businesses compete, win and succeed. We provide the technology, software and local business automation tools small business owners need to better manage their time, communicate with clients, and get paid, so they can take control of their business and be more successful. We support businesses across the U