Customer Success AI Operations Lead

BitSight Technologies•Boston, MA

1d•$78,980 - $117,000•Remote

About The Position

Bitsight is a cyber risk management leader transforming how companies manage exposure, performance, and risk for themselves and their third parties. Companies rely on Bitsight to prioritize their cybersecurity investments, build greater trust within their ecosystem, and reduce their chances of financial loss. Built on over a decade of technological innovation, its integrated solutions deliver value across enterprise security performance, digital supply chains, cyber insurance, and data analysis. We invented the cyber ratings industry in 2011 Over 3000 customers trust Bitsight Over 750 teammates are dispersed throughout Boston, Raleigh, New York, Lisbon, Singapore, and remote We are building an AI-native Customer Success operating model from the ground up, and we’re looking for a hands-on builder/operator to help bring it to life. This role sits at the intersection of Customer Success, operations, AI, data, systems, and workflow design. The ideal candidate can take a clear business vision, rapidly prototype solutions, gather feedback, iterate quickly, and turn early ideas into scalable workflows that help the CS team operate with more speed, intelligence, and consistency. This is not a traditional CS Ops administration role or a pure strategy role. This person will be expected to build. You’ll work closely with CS leadership to design and implement AI-enabled workflows across lifecycle management, customer health, risk detection, renewal readiness, executive engagement, EBR/QBR preparation, digital engagement, support deflection, and CSM productivity. The right person is technically curious, highly resourceful, comfortable with ambiguity, and genuinely excited by the opportunity to use AI to redesign how Customer Success work gets done.

Requirements

2–6+ years of experience in Customer Success Operations, Revenue Operations, Support Operations, Technical Account Management, Solutions Consulting, Customer Success, Technical Support, or a similar role.
Demonstrated experience using AI tools to build practical workflows, automations, internal tools, summaries, agents, or business processes.
Strong builder/operator mindset with a bias toward fast prototyping and iteration.
Comfort working with CRM, CS, support, revenue, or data systems.
Ability to take loosely defined ideas and turn them into structured execution.
Strong systems thinking across process, data, tools, and user experience.
Comfortable operating in ambiguity and making pragmatic tradeoffs.
Strong cross-functional communication and documentation skills.
High ownership, attention to detail, and willingness to incorporate feedback quickly.

Nice To Haves

Hands-on experience with Salesforce, Gainsight, Gong, Clari, Zendesk, Slack, Zoom, Google Workspace, or similar GTM tools.
Experience with Claude, Claude Code, ChatGPT, Gemini, Cursor, Replit, or other modern AI tools.
Experience with automation tools such as Zapier, Make, Workato, n8n, Tray.io, or similar platforms.
Familiarity with Snowflake, SQL, data warehouses, BI tools, or data modeling concepts.
Experience building workflows that use CRM, call, support, product, or customer data.
Customer-facing experience in CS, Support, TAM, Solutions Consulting, or Technical Support.
Basic scripting, API, or low-code/no-code automation experience.
Experience administering or configuring GTM systems.

Responsibilities

Build AI-powered workflows, automations, prompts, templates, and tools that reduce manual work and improve CS execution.
Prototype and scale workflows such as automated EBR/QBR decks, renewal briefs, customer summaries, risk narratives, meeting prep, and next-best-action recommendations.
Help operationalize the CS operating model, including lifecycle stages, health and risk models, renewal readiness, executive engagement, customer prioritization, and value tracking.
Partner with CS, RevOps, Data, Support, Product, and other teams to connect the right data into the right workflows.
Work across systems such as Salesforce, Gainsight, Clari, Gong, Zendesk, Snowflake, Slack, Zoom, Google Workspace, Claude, ChatGPT, and other AI/automation tools.
Establish prompt structures, QA checks, feedback loops, and documentation to ensure AI outputs are useful, accurate, and scalable.
Gather feedback from CSMs and leaders, iterate quickly, and continuously improve workflows based on real team usage.
Help CSMs spend less time on manual reporting, prep, and coordination, and more time on high-value customer engagement.