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)
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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.
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Pilot AI/automation use cases (e.g., QA assistance, content checks, workflow orchestration) with clear success criteria and guardrails.
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Partner across teams to surface real challenges and turn them into opportunities that move our Strategic Objectives and KPIs.
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Translate operational and client needs into simple, adoptable technical solutions that improve accessibility, quality, and efficiency.
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Lead client-facing demos as the subject-matter expert, showcasing value and gathering feedback to inform the next iteration.
Core Systems & Automation
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Map and rationalize our tech stack (SSO, hostings and domains, PM/TMS/CAT, QA tools); close redundancy, reduce cost, and document data flows.
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Automate key handoffs across teams (e.g., intake → PM → QA → billing) using APIs/low-code tools; publish SOPs.
IT Infrastructure & Security
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Keep our foundations reliable and secure: endpoint management, backups tested, access reviews, incident response, turn findings into improvements, collaborate with external IT support partners.
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Own day-to-day support excellence: meet or beat response/resolution targets, with clear communications and simple self-service.
Partnering & Enablement
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Be the technical liaison with vendors, partners and platform providers; get the best from our tools.
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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).
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Fully bilingual in English and Spanish.
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Comfortable across identity/SSO, device management, SaaS administration, and workflow automation (APIs, scripts, Notion, or similar).
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Pragmatic understanding of security practices (incident response, basic risk management).
- Nice to have: exposure to localization/accessibility tech, basic Python/JS.
- A Continuous Improvement Mindset (Efficiency & Adaptability)
How we work
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💻 Remote-friendly, Work From Anywhere. We collaborate with smart overlap between team members; we value outcomes over hours.
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🧠Strategic Objectives & KPIs. We align on clear goals, review regularly, and celebrate learning as much as delivering.
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🧘♀️ Wellbeing Program. Support to keep you energized and balanced.
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🌴Extended PTO. Time to rest and reset—because recovery fuels great work.
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🎂Birthday day off. It’s your day—go enjoy it.
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📚Continuous learning. Real opportunities to grow skills and careers ( Winnow Learning).
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🌟 Purpose-driven culture. Your ideas matter here, and your impact is real.
The basics
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Level: Individual Contributor (no direct reports)
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Reports to: Ops Manager
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Location: Remote (preference for overlap with Europe ±3h)
- Type: Full-time
