Sales Development Representative

**Rubie** Sales Development Representative; $70–80K base / $110–120K OTE + equity + commission; New York City (On-site)

**About Company** Rubie helps software companies win deals by making data migration automatic. Its computer-use and browser-use agents log into whatever system of record a customer is leaving, pull out and clean the data, and move it into the new system — turning what used to be weeks of manual work into a near one-click, end-to-end migration. Rubie sells to the software vendors themselves (the new CRM, ATS, or ERP), helping them rip customers off a competitor. It's a "data sovereignty" mission: your data shouldn't be held hostage by the software you're leaving.

Rubie is growing fast. It raised a $15M Series A earlier in 2026, is scaling revenue sharply (roughly a 10x year), and just closed its first near-seven-figure deal. Average deal size has climbed from ~$50K to ~$85–90K this quarter and is trending past $100K, while net revenue retention runs ~190% — once customers cross an initial trust gap, they hand Rubie their entire migration and post-sales data function. The beachhead market is vertical SaaS (software for fitness studios, dental practices, property managers, and the like), with a longer-term TAM of any software company that has a competitor.

The team is ~20 people, deliberately senior and high-performing. Founder/CEO Jimmy McDermott has been a technical and product leader his whole career — previously CTO and co-founder of a K-12 edtech startup he scaled and sold — and Rubie is the second-time founder's answer to the biggest problem he hit there. HQ is in NYC (Flatiron, near Eataly), in-person five days a week.

**About the Role** An SDR seat on Rubie's fast-scaling GTM team, working side-by-side with the sales team to build pipeline across Rubie's core verticals and partnering with AEs on new business. Rubie's outbound engine is already highly productive and the pipeline is outstripping capacity, so this role plugs into a proven motion — sourcing and qualifying roughly 10–12 qualified meetings a month after a 4–6 week ramp. The hire partners across the AE team on a shared basis for now, with a head of sales and a dedicated SDR manager joining over the next couple of months.

**Responsibilities** - Run outbound prospecting across email, phone, and LinkedIn to generate qualified meetings for the sales team. - Test and iterate on messaging, sequences, and targeting across Rubie's core verticals (legal tech, property management, edtech, fintech, and more). - Build targeted prospect lists, research accounts, and identify trigger events that signal a company needs data-migration help. - Lead qualification calls to understand prospects' migration pain points, timelines, and decision process; convert cold and warm leads into qualified meetings for AEs. - Partner with sales on lead quality and campaign performance; build working fluency in data-migration concepts (extraction, transformation, ingestion, delta migrations, go-live cutovers) to speak credibly to technical buyers.

**Required Skills** A. Around 1 year of outbound experience (within a 0–3 year range) with a proven playbook — can ramp fast, rather than a raw 0–1 to train from scratch. B. Exceptional written and verbal communication — can distill technical concepts into clear, conversational messaging. C. Comfortable with high-volume outbound and the organizational discipline to manage it without detail slipping. D. Analytical, experiment-driven approach to outreach — tests sequences and targeting and uses data to decide what works.

**Bonus Skills** - Experience prospecting into technical buyers (engineering, ops, or implementation leaders). - Familiarity with outbound tooling (Apollo, Outreach, HubSpot, LinkedIn Sales Navigator, or similar).

**Logistical Info** - Location: New York City, in-person at the Flatiron office (near Eataly) 5 days/week — no exceptions. - Compensation: $70–80K base / $110–120K OTE depending on seniority, plus meaningful equity and uncapped commission.

**Ideal Background** - Open to any background — Jimmy prioritizes hustle and grind over pedigree for this SDR hire (no specific target-company list, unlike the AE search). - Sweet spot is ~1 year of outbound experience with a proven playbook (vs. a raw 0–1 to train). - Verticals Rubie sells into: legal tech, property management, edtech, fintech. - The jumpiness filter applies across Rubie roles: evidence of compounding/progression matters more than logos or schools.

**Green Flags** - High-energy, grind-it-out communicator who can hold a qualification call and speak credibly to technical buyers. - Evidence of compounding — progression or tenure rather than job-hopping. - Experiment-driven; iterates on sequences and targeting using data.

**Red Flags** - Jumpiness — a string of short stints with no evidence of compounding (Jimmy's number-one filter across roles). - Can't articulate outbound metrics or what worked and didn't in past sequences. - Needs a structured, hand-held environment; can't operate in a fast-changing early-stage team.

**Interview Process** 1. 30-min screen with an AE on the team. 2. 30-min with the CEO (Jimmy). 3. On-site with a case study.