Systems Specialist
Purpose: Improve lives through accessible information by scaling the tech that powers how Winnowers work and how Customers experience us.
About Win & Winnow
We’re a global team of Winnowers making information accessible. We blend content management services, digital accessibility, and smart tech to remove communication barriers—guided by our values: Transparency, Gratitude, Commitment, Accountability, Respect, Excellence.
You might be a fit if you… love turning real user problems into simple, secure, automated solutions; enjoy partnering across teams; and get energy from piloting AI responsibly to boost accessibility and quality.
What you’ll do (outcomes, not just tasks)
Strategy & Innovation (AI + Accessibility)
- Ship a 12-month tech & innovation roadmap tied to company strategic objectives and KPIs—prioritizing projects that improve accessibility service offer, quality, and delivery speed.
- Pilot AI/automation use cases (e.g., QA assistance, content checks, workflow orchestration) with clear success criteria and guardrails.
- Partner across teams to surface real challenges and turn them into opportunities that move our Strategic Objectives and KPIs.
- Translate operational and client needs into simple, adoptable technical solutions that improve accessibility, quality, and efficiency.
- Lead client-facing demos as the subject-matter expert, showcasing value and gathering feedback to inform the next iteration.
Core Systems & Automation
- Map and rationalize our tech stack (SSO, hostings and domains, PM/TMS/CAT, QA tools); close redundancy, reduce cost, and document data flows.
- Automate key handoffs across teams (e.g., intake → PM → QA → billing) using APIs/low-code tools; publish SOPs.
IT Infrastructure & Security
- Keep our foundations reliable and secure: endpoint management, backups tested, access reviews, incident response, turn findings into improvements, collaborate with external IT support partners.
- Own day-to-day support excellence: meet or beat response/resolution targets, with clear communications and simple self-service.
Partnering & Enablement
- Be the technical liaison with vendors, partners and platform providers; get the best from our tools.
- Enable Winnowers with short, accessible training (Winnow Learning) and job aids so changes stick.
Your experience & strengths
- 3–5 years in a hands-on tech/IT/solutions role (SMB or scale-up environment).
- Fully bilingual in English and Spanish.
- Comfortable across identity/SSO, device management, SaaS administration, and workflow automation (APIs, scripts, Notion, or similar).
- Pragmatic understanding of security practices (incident response, basic risk management).