BitSight Technologies

Customer Success AI Operations Lead

BitSight Technologies$78K — $117K *
US-AnywhereRemote in Boston, MA
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 2-6+ years in Customer Success Operations, Revenue Operations, or related fields.
  • Proven experience using AI tools for workflow automation and building processes.
  • Builder/operator mindset focused on rapid prototyping and iteration.
  • Ability to execute loosely defined concepts into structured plans.
  • Strong systems thinking across tools, processes, and user experiences.
  • Experience communicating clearly across cross-functional teams.
  • Detail-oriented with strong ownership and adaptability to feedback.

Responsibilities

  • Build AI-powered workflows and tools to enhance CS efficiency.
  • Prototype scalable workflows for customer engagement and reporting.
  • Operationalize CS model including health, risk, and renewal management.
  • Collaborate with cross-functional teams to integrate data into workflows.
  • Work with various systems like Salesforce and AI tools to streamline processes.
  • Establish QA and feedback mechanisms for AI outputs.
  • Iterate and enhance workflows based on team feedback.

Benefits

  • Medical, dental, and vision insurance coverage.
  • Paid parental leave and flexible time off options.
  • 401(k) plan with contributions from both employee and employer.
  • Life and disability insurance benefits.
  • Tuition reimbursement for continued education.
Full Job Description


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.

What You'll Do
  • 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.


What Success Looks Like

In the first 90 days, you will:
  • Learn the CS operating model, current workflows, core systems, and biggest pain points.
  • Identify the highest-impact opportunities for AI and automation across the CS lifecycle.
  • Ship several practical AI-enabled workflows that reduce manual CSM effort.
  • Build repeatable prompt, QA, and feedback processes.
  • Help operationalize core lifecycle, health, risk, renewal, or EBR/QBR workflows.
  • Demonstrate measurable impact on CSM productivity, consistency, or customer-facing output quality.

Over time, you will help build a scalable AI and automation layer across the customer lifecycle and establish CS Ops as a strategic engine for scale, efficiency, and customer impact.

What We're Looking For
  • 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.
Preferred Experience
  • 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.


The anticipated hiring base salary range for this position is US$78,980 to $117,000 annually for US-based employees. This range reflects the minimum and maximum target for new hire salaries for the position across all US locations, is based on a full-time work schedule, and is Bitsight's good faith estimate as of the date of this posting. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training.

In addition to base salary, this role is eligible for participation in a bonus or commission plan and an equity grant. Bitsight also offers a competitive benefits package, including but not but limited to medical, dental, and vision insurance; paid parental leave; flexible time off; a 401(k) plan with employee and company contribution opportunities; life and disability insurance; and tuition reimbursement.

About BitSight Technologies

BitSight Technologies is a cybersecurity ratings company that provides cybersecurity risk management solutions to organizations. The company's platform uses a data-driven approach to assess the security posture of organizations and their vendors. BitSight's platform is used by companies to manage third-party risk, benchmark performance against industry peers, and improve their overall cybersecurity posture. The company was founded in 2011 and is headquartered in Boston, Massachusetts.
Learn more about BitSight Technologies
Size
500 employees
Industry
Founded
2011

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