Technical Support Specialist (CSM Track)

Customer Success Team | Reports to Head of CS | East Coast, US-based, Fully Remote

About Guidebook

Guidebook is the leading mobile app platform for events and engagement, with a strong focus on higher education. Universities and colleges across North America use Guidebook to run admissions events, orientation programs, and campus engagement that bring their student communities together. We are a small, ambitious team building a category-defining product, and we love working with people who care about education, technology, and craft.

About the Job

Our Customer Success team is small, technical, and ambitious, and we are looking for two Technical Support Specialists to join us — both on an expected path to becoming Customer Success Managers within 3 to 12 months.

Here is what that means in practice. You will start by owning the technical support function alongside our CS Technical Lead, and one other Specialist hired at the same time. You will become an expert in our Builder CMS, manage and improve our AI-first support stack — your job is to make it smarter, handle what it cannot, and spot patterns — to resolve customer tickets quickly and warmly. Within 3 months, one of the two Specialists will move into a CSM role, taking on a portfolio of top-tier customers. Within 12 months, the second Specialist will follow. By that point, both of you will be running customer portfolios, with our AI tooling carrying the support load behind you.

We are being upfront about this trajectory because we want you to want it. If you are looking for a long-term technical support role, this is not the right fit. If you are someone who loves figuring out how things work, takes pride in solving customer problems, and wants to grow into a customer-facing strategic role — where you’ll be on a lot of video calls — at a small, fast-moving company, keep reading.

You will work directly with our Head of CS, our CS Technical Lead, and our CSM, and you will collaborate cross-functionally with sales, product, and engineering. The Customer Success function is critical to Guidebook's growth, and this hire is a key part of how we are scaling it.

Who You Are

• You are genuinely curious about how things work. When something breaks, your instinct is to figure out why, not just patch it.
• You take ownership. You do not wait to be told. If you spot a gap in our knowledge base, a recurring ticket type that should be automated, or a customer at risk, you flag it and start working on it.
• You are a real communicator. You can write a clear, warm response in three sentences. You can hop on a video call with a frustrated customer and leave them feeling better.
• You want to grow into a customer-facing role. The whole point of this hire is the trajectory, and you are excited about being in meetings or on the phone with customers all day in 3 to 12 months.
• You see AI as a tool, not a threat. You are excited about making our AI support stack smarter, and you have strong instincts for when a human conversation matters more than an automated one.
• You thrive in a small, fast-moving company. You find quick decisions and visible work energizing rather than chaotic.
• You disagree well. You can push back on a teammate respectfully, hear pushback in return, and keep the conversation moving forward.
• You are happy in a fully remote environment and are comfortable managing your own time.

Characteristics of the Ideal Candidate

• 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 — you know what good support looks and feels like.
• 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).
• Tooling experience is a plus, but not required, we will train. Useful exposure includes Salesforce, Zendesk or Intercom, Slack, Jira, and any modern CMS.
• Curious about AI tooling and willing to use it to work smarter. Guidebook is an AI-forward business, and our support stack is AI-first by design.
• Familiarity with the events industry, higher education, or association space is a bonus but not required.

Key Responsibilities

Technical Support and AI Tooling

• Own a queue of customer tickets, resolving issues, escalating thoughtfully, and writing clear, warm responses.
• Manage and improve our AI support stack. Review what it answered, what it got wrong, and feed that back into making it better over time.
• Become fluent in Guidebook's Builder CMS and the broader product suite.
• Spot patterns in what customers struggle with and surface them to product, engineering, and CS.
• Contribute to our knowledge base and internal documentation. If you fix something twice, you write it up.
• Coordinate with our CS Technical Lead on broader tech stack work as you grow into the role.
• Minor weekend support responsibilities for escalated tickets.

Customer Relationships (Growing Over Time)

• Build relationships with customers through ticket-based conversations in your 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 your accounts and work with sales partners to act on them.
• Drive Net Revenue Retention on your accounts as a CSM, with compensation tied to your portfolio's performance.

Cross-Functional Coordination

• Act as a connector between customers, product, engineering, and CS.
• Brief the team on emerging customer issues, product gaps, and patterns worth investing in.
• Partner with sales on renewal and upsell motions as you grow into CSM responsibilities.
• Mentor the next round of Specialists hired behind you once you are in the CSM seat.

Continuous Improvement

• Keep raising the bar on our support quality, response times, and AI accuracy.
• Help shape the playbook for how this role evolves, what we automate, what we keep human, and what we hand off as the team grows.
• Contribute to a culture of honest feedback, fast iteration, and shared ownership.

Your First 12 Months

Within 3 Months

• Achieve a strong working knowledge of Guidebook's Builder CMS, our AI support stack, and our customer base.
• Own a queue of customer tickets, resolving the majority without escalation.
• Make meaningful improvements to our AI support stack's accuracy and coverage.
• Build collaborative working relationships across CS, Sales, product, and engineering.
• One of the two Specialists hired into this role will move into a CSM seat at this point.

Within 6 Months

• If you have moved into the CSM role: have a clear handle on your portfolio, run regular customer calls to ensure strong customer relationships, and directly impact NRR.
• If you are still in the Specialist role: be the resident expert on our platform and AI tooling, work cross collaboratively to ensure the knowledgebase and tech stack continues to improve, and visibly prepare for your own move to CSM.
• Build strong working relationships with key customers.
• Run a clean cadence of pattern reporting back to product and engineering.

Within 12 Months

• Be a trusted face at Guidebook's flagship higher education and events customers.
• Help establish the playbook for how this role evolves and how we hire the next round.
• Create clear pathways for growth into more senior CS roles within Guidebook.

Key Performance Indicators

Success in this role will be measured against support quality, platform expertise, and your readiness to move into the CSM seat. Specific targets will be set with the Head of CS on joining and reviewed monthly.

• Support Quality: First response time and resolution time on assigned tickets, customer satisfaction (CSAT) scores, escalation rate, quality review scores on written responses
• AI Stack Performance: AI system solve rate improvement over time, accuracy of AI responses on reviewed tickets, knowledge base coverage and freshness, reduction in repeat ticket volume
• Platform Expertise: Demonstrable Builder CMS fluency by month 2, ability to run a customer-facing platform walkthrough by month 3, internal certification on core product areas
• CSM Readiness: Quality of customer interactions on video and live channels, ownership of cross-functional escalations, depth of customer context and account knowledge, readiness signals reviewed monthly with the Head of CS
• Post-Transition (CSM Seat): Net Revenue Retention on assigned portfolio, renewal rates, expansion pipeline, customer health scores

Compensation and Logistics

• Annual On Target Earnings (OTE): $50,000-60,000, depending on experience, with growth tied to your move into the CSM role.
  • Variable paid quarterly will be between 10-20% of OTE
• Fully remote role, US-based, East Coast required.
• Benefits package in line with Guidebook's standard offering: 100% paid medical, dental, and vision; short-term and long-term disability; unlimited vacation; 401(k) with matching; stock options; MacBook and home office setup; annual company retreat.

What to Provide with your Application

• Resume
• Cover letter
• A video answering the following:
  • Tell us about a customer or user you helped that you're especially proud of. What was the situation, and how did you make it better?
  • What's a school, conference, or event experience you'll never forget? What made it great?
  • Keep it under 3 minutes. We're more interested in how you talk about this than how polished it is. Phone, webcam, or Loom is fine. Please submit your video using this Google Form link.

Equal Opportunity Employer

At Guidebook, we're committed to cultivating an inclusive work environment for everyone – and we know that's best achieved, in part, with a diverse workforce. We're working on increasing diversity across the company. If you're looking to join a team that is smart, highly motivated, and also values work/life balance, we can't wait to hear how you can add to our growing culture!

We are an Equal Opportunity Employer and do not discriminate against any employee or applicant for employment because of race, colour, sex, age, national origin, religion, sexual orientation, gender identity and/or expression, status as a veteran, and basis of disability or any other federal, state or local protected class.