Technical Support Specialist (CSM Track)

Guidebook•Raleigh, NC

9d•$50,000 - $60,000•Remote

About The Position

Guidebook is seeking two Technical Support Specialists for its Customer Success Team, with a clear trajectory towards becoming Customer Success Managers within 3 to 12 months. This role involves owning the technical support function, managing and improving an AI-first support stack, and resolving customer tickets. The position is fully remote and US-based, requiring candidates to be comfortable with a fast-paced, small-team environment and have a genuine curiosity for technology. The ideal candidate is a strong communicator, takes ownership, and is excited about growing into a customer-facing strategic role.

Requirements

1+ years of professional experience in SaaS support, customer success, or a similar customer-facing role.
Hands-on experience working tickets and talking to customers.
Strong written and verbal communication skills.
Comfortable working with a remote team across multiple time zones.
Detail-oriented, with a strong ability to track multiple conversations, customers, and priorities at once.
Comfortable with public-facing tasks (running a video call, hosting a customer training, walking someone through a platform).
Curious about AI tooling and willing to use it to work smarter.
Genuine curiosity about how things work.
Takes ownership; does not wait to be told.
A real communicator; can write a clear, warm response in three sentences.
Wants to grow into a customer-facing role.
Sees AI as a tool, not a threat.
Thrives in a small, fast-moving company.
Disagrees well; can push back respectfully and hear pushback in return.
Happy in a fully remote environment and comfortable managing own time.

Nice To Haves

Tooling experience is a plus, but not required, we will train.
Useful exposure includes Salesforce, Zendesk or Intercom, Slack, Jira, and any modern CMS.
Familiarity with the events industry, higher education, or association space is a bonus but not required.

Responsibilities

Own a queue of customer tickets, resolving issues, escalating thoughtfully, and writing clear, warm responses.
Manage and improve our AI support stack, reviewing its performance and feeding back improvements.
Become fluent in Guidebook's Builder CMS and the broader product suite.
Spot patterns in customer struggles and surface them to product, engineering, and CS.
Contribute to our knowledge base and internal documentation.
Coordinate with the CS Technical Lead on broader tech stack work.
Handle minor weekend support responsibilities for escalated tickets.
Build relationships with customers through ticket-based conversations in the first 3 months.
Take on a portfolio of customer accounts as you transition into the CSM role.
Run onboarding calls, customer check-ins, and renewals as a CSM.
Identify growth opportunities within accounts and work with sales partners.
Drive Net Revenue Retention on accounts as a CSM.
Act as a connector between customers, product, engineering, and CS.
Brief the team on emerging customer issues, product gaps, and patterns.
Partner with sales on renewal and upsell motions.
Mentor the next round of Specialists hired.
Keep raising the bar on support quality, response times, and AI accuracy.
Help shape the playbook for how this role evolves.
Contribute to a culture of honest feedback, fast iteration, and shared ownership.