Contract Operations Systems Analyst

Over 9,000 companies — from scrappy startups to global brands — use our platform to send billions of emails, push notifications, in-app messages, and SMS every day. Customer.io powers automated communication that people actually want to receive. We help teams send smarter, more relevant messages using real-time behavioral data.

Hi, my name is Bill Miksich, VP of Operations at Customer.io, and I'm looking for a contract Operations Systems Analyst to join our Strat Ops team.

The pace of AI model releases and pricing shifts requires dedicated bandwidth to evaluate options before they turn into cost or capability decisions. This includes commercial models, open source models, and on-prem alternatives. Right now that research burden falls to already-stretched senior staff. We're facing a worst case AI spend scenario approaching $6.0M annualized, and this role exists to get ahead of it.

The remaining scope of the role covers smaller operational vendor projects, starting with our SMS and messaging vendor evaluation work. This is a contract engagement. We want to validate the value of dedicated AI cost and model optimization work before committing to permanent headcount.

• Rigor over instinct — you evaluate vendors and models on cost, capability, and risk, not on which one has the best sales pitch.
• Independent execution — you take a broad, ambiguous mandate and turn it into a structured evaluation without needing much direction.
• Clear communication — you can explain a model pricing tradeoff to a technical lead and a finance stakeholder without losing either of them.
• Comfort with moving targets — AI model releases and pricing change fast; you keep the evaluation framework current instead of treating it as a one-time project.

• Evaluate AI model options as they come to market — commercial, open source, and on-prem — and build a repeatable framework for assessing cost, capability, and security tradeoffs (75% of role).
• Build and maintain cost models comparing API-based pricing against flat subscription alternatives for heavy AI users.
• Validate different approaches to controlling AI cost exposure, giving stakeholders data to act on instead of ad hoc decisions.
• Keep the evaluation framework current as models and pricing shift, including tracking renewal timing on AI vendor agreements.
• Support smaller-scope vendor evaluation projects, starting with SMS and messaging vendors — compliance capability, aggregator relationships, and pricing structure (25% of role).

• Experience evaluating software vendors, ideally including AI platforms or communications/messaging platforms
• Comfort building cost models and structured vendor comparison frameworks
• Able to work independently with senior stakeholders across technical and operations teams
• Experience in a B2B SaaS environment preferred
• Familiarity with SMS or messaging compliance is a plus but not required

We believe in transparency. Starting agreement for this role is $75/hr-$85/hr USD (or equivalent in local currency) depending on experience and subject to market rate adjustment.

No gotchas, no trick questions - just a clear, human process designed to help both of us make an informed decision.

1. 30-minute video call with a Recruiter
2. 45-minute video call with the Hiring Manager

All final candidates will be asked to complete a background check and employment verifications as part of our pre-employment process.

Customer.io recognizes the stifling impact of systemic injustice on diverse communities. We commit to using our influence to increase inclusion and equity within the tech industry. We strive to build an inclusive team culture, implement bias-free hiring practices, and develop community partnerships to expand our global impact.

Zoom is the only video conference platform that we use, virtual interviews will be conducted using the video capability (i.e., not via the chat), and offers will be extended in writing on official Customer.io letterhead. Please be vigilant in all of your job search activity, and if you have any questions please contact [email protected].

Check out our careers page for more information about why you should come work with us! We believe in empathy, transparency, responsibility, and, yes, a little awkwardness. If you’re excited by what you read — apply now.