Chitresh Singh

Customer Success Leader | Helping B2B Teams Drive Retention, Revenue & Relationships | Advocate for AI-Driven Productivity | Ex-Accenture | MBA

Toronto, Ontario, Canada

About

I’m a customer success leader with 10+ years of experience driving growth, retention, and operational excellence across B2B SaaS, enterprise software, and digital transformation initiatives. At Chili Piper, I’ve worked closely with mid-market and enterprise customers to optimize outcomes and drive adoption, consistently exceeding retention and expansion targets. Previously, I led digital transformation efforts for public and private organizations, and managed multi-million-dollar portfolios across health tech and higher ed. I’m passionate about blending strategy with empathy — aligning teams, processes, and technology to create customer experiences that truly scale. I’m especially interested in how AI is reshaping customer-facing teams enabling us to focus more on relationships, not just tasks. When I’m not working with clients or mentoring newer CS professionals, I write about customer success, retention, onboarding, and the future of CS ops. My goal is to help CS leaders do more with less, and build high-leverage customer engines that work even when you’re not in the room. Let’s connect if you're building something meaningful, scaling a CS team, or exploring how automation and AI can support human-first customer relationships.

Experience

  • Senior Customer Success Manager at Chili Piper
    Jul 2021 - Present · 5 yrs

    Managing customer accounts ranging from small, mid-market to enterprise customers to drive product adoption, retention, and expansion. 🥇 #1 in CSQO-sourced revenue and onboarding completions company-wide 🥇 Delivered $81k+ in expansion revenue (mid-market) 🥇 Retention leader: 96% account retention across portfolio 🥇 NPS: 100% Promoters, 80% scored 10/10 🥇 Utilization consistently 2.5x target

  • Customer Success Manager at Crossover
    Jan 2019 - Jun 2021 · 2 yrs 6 mos

    Managed and owned a large portfolio ($15m+) of Aurea's key customers from SMEs to large enterprises. Managed all projects, relationships, onboarding, trainings, and support activities for all these customers.

  • Mohawk College (6 yrs)
    • Professor
      Jan 2018 - Dec 2018 · 1 yr

      Taught Business and Technology programs 🏆 Judge - Skills Ontario Competition

    • Senior Project Manager
      Aug 2016 - Dec 2018 · 2 yrs 5 mos

      Lead a multi-million-dollar portfolio of software projects for clients such as Ministry of Health and Long-Term Care (MOHLTC), Canada Health Infoway, eHealth Ontario, IBM Canada, and Hamilton Health Sciences. Lead teams with 15+ professionals including project coordinators, software developers, analysts, UI/UX designers, QA, privacy & security and industry experts to design and build digital health solutions for both consumers and healthcare providers in Canada. 🏆 Mohawk College Staff Leadership Program 🏆 Mohawk College Staff Mentor

    • Business Analytics Consultant
      Jan 2013 - Aug 2016 · 3 yrs 8 mos

      Spearheaded the implementation of a college-wide analytics and reporting culture. Setup systems and processes that generated insights and recommendations to the management team make fact-based decisions. 🏆 Nominated for the President’s Award of Excellence.

  • Consultant at Accenture
    2009 - 2011 · 2 yrs

    Worked on multiple software development, application support, data management and business intelligence projects for Accenture's global clientele. 🥇 Accenture Coding Competition Winner (1st place) 🏆 Received Accenture Numero Uno Award for Excellence in Business Operations and Contribution to Delivery Excellence.

  • Co-founder and CTO at ApniGaddi.com
    2008 - 2009 · 1 yr

    Co-founded ApniGaddi.com, India's first online car market that targeted youth to buy/sell used cars online. Designed an easy-to-use website where people could register and post ads or search for cars that matched their budget and preferences. The value proposition was to promote and ensure each posted ad contained car pictures taken from 4 different angles so that buyers take interest and trust the authenticity of posted ads.