Pragmatico is a mid-market AI transformation company. We embed a fractional Transformation Partner and delivery team inside client organizations to drive real, behavioral AI adoption - not slideware. We're building our go-to-market engine, and this is one of our first dedicated outbound hires. You'll have outsized influence on how we build top-of-funnel and a clear path to grow with the team.
As our Sales Development Representative, you own outbound pipeline as we scale: you research target accounts, run multichannel prospecting into mid-market decision-makers, and book qualified first meetings for our account executives. You're the tip of the spear - the first voice a prospect hears from Pragmatico - and the quality of pipeline you build directly drives our growth.
Prospect into target accounts daily across phone, email, and LinkedIn - with research and personalization, not spray-and-pray.
Book qualified first meetings that our AEs accept and hold, using agreed qualification criteria.
Own your pipeline hygiene in HubSpot: log every touch, keep records clean, report your numbers honestly.
Learn and speak credibly to Pragmatico's AI transformation story and the operating pain points of mid-market buyers.
Partner tightly with the AE team and marketing to sharpen messaging, target lists, and hand-offs.
Bring signals back: what's landing, what's not, which accounts and messages are working.
1–3 years of outbound SDR/BDR experience in B2B, ideally selling a considered or consultative product/service.
A track record of booking qualified meetings and comfort on the cold phone.
Strong written skills: you can write a short, relevant, personalized outreach that gets replies.
Fluency (or fast learning curve) with a cadence/sequencing tool and CRM (HubSpot a plus).
Curiosity about how AI is changing how businesses operate - you don't need to be technical, but you need to care.
Grit, coachability, and honesty. You hit the phones without being chased and you tell the truth in the CRM.
Bonus: exposure to insurance, professional services, or the mid-market; experience selling into executives.
On-target earnings ~$75–95K - competitive base plus uncapped variable tied to qualified meetings and sourced pipeline.
Fully remote within the US.
Early-team role with a real path to AE and clear influence on how we build GTM.
Why Pragmatico
Pragmatico guides mid-market companies to turn AI investment into measurable business value by leading with culture change and adoption. We work with companies where AI transformation is a CEO-level priority, and we stay with them through the full journey. Our clients have achieved measurable business outcomes that show up in the numbers and hold up in front of a board.
This role puts you at the center of that work. You are the person in the room when the transformation actually happens. The clients you train become the proof that Pragmatico's methodology works.
Learn more at www.pragmatico.ai.
Pragmatico is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to gender, age, race, religion, or any other classification that is protected by applicable law.
Skills Required
- 1-3 years outbound SDR/BDR experience in B2B
- Proven track record booking qualified meetings and comfort with cold calling
- Strong written communication and personalized outreach skills
- Fluency or quick learner with cadence/sequencing tools and CRM
- Experience with HubSpot
- Curiosity about AI and how it changes business operations (not technical)
- Grit, coachability, self-motivation, and honesty in CRM reporting
- Exposure to insurance, professional services, mid-market, or selling into executives
What We Do
Pragmatico is an AI cultural transformation company that helps mid-market companies become AI-native. They provide a systematic approach to AI adoption, encompassing vision, policy, psychological safety, and training to embed AI as a core organizational capability, ensuring the transition is human, practical, and permanent.
