Sr Service Design Specialist

About Checkr
Checkr is building the data platform to power safe and fair decisions. Established in 2014, Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100,000 customers including DoorDash, Coinbase, Lyft, Instacart, and Airtable.

We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

About the team/role

We are seeking a skilled and detail-oriented Senior Service Design Specialist to join our Service Design team. This role is central to managing and optimizing our conversational AI agents across multiple modalities, directly impacting customer experience and operational efficiency. The ideal candidate will have hands-on experience with conversational AI platforms, a strong understanding of conversation design principles, and the ability to analyze performance data to drive continuous improvement. This role requires someone who is curious, adaptable, and passionate about leveraging AI to deliver seamless, human-centered support experiences.

What you’ll do

• Lead the development, optimization, and ongoing management of conversational AI agents across modalities, ensuring consistent performance and user experience.

• Own the end-to-end lifecycle of assigned AI agents, including prompt engineering, conversation design, testing, and deployment.

• Drive measurable improvements in agent performance through analysis of key performance indicators and conversation analytics.

• Partner with cross-functional teams to identify automation opportunities and implement solutions that reduce contact volume while maintaining service quality.

• Develop and maintain comprehensive documentation for AI agent workflows and processes.

• Monitor and troubleshoot AI agent behavior, diagnosing issues across conversation flows and escalating technical issues as needed.

• Implement and iterate on dynamic response content, including conditional logic, personalization, and multimedia elements within conversational interfaces.

• Lead special projects as required to support evolving AI capabilities and business needs.

What you bring

• 3-5 years of experience in conversational AI, knowledge management, chatbot administration, or similar roles managing customer-facing digital channels.

• Hands-on experience with conversational AI platforms and understanding of NLU/NLP concepts.

• Proficiency in conversation design principles, including intent mapping, utterance training, and fallback strategies.

• Strong analytical skills with the ability to interpret conversation logs, performance dashboards, and customer feedback to drive optimization.

• Excellent written communication skills and ability to craft clear, concise bot responses for diverse audiences.

• Proven ability to collaborate cross-functionally and translate business requirements into actionable solutions.

• Comfort navigating ambiguity and managing multiple priorities in a fast-paced environment.

• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What you get:

• A fast-paced and collaborative environment

• Learning and development allowance

• Competitive compensation and opportunity for advancement

• 100% medical, dental and vision coverage

• Unlimited PTO policy

• Monthly wellness stipend, home office stipend

Pay Transparency Disclosure

One of Checkr’s core values is Transparency. To live by that value, we’ve made the decision to disclose salary ranges in all of our job postings. We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website.

On-target Earnings OR Base Salary range (Denver, CO)
$90,000—$112,000 USD

At Checkr, we believe a hybrid work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO, San Francisco, CA, Nashville, TN, and Santiago, Chile. Individuals are expected to work from the office 3 days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.

Equal Employment Opportunities at Checkr
Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.

Applicant Privacy Policy
If you are a California resident or are located in Alberta or British Columbia, our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process.

*Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g., [email protected] or [email protected]).