Technical Support Specialist

About EasyLlama

EasyLlama is on a mission to end checkbox compliance. We started by reinventing compliance training with engaging, bite-sized, mobile-first learning instead of outdated, one-size-fits-all courses. Today, we're building an AI-powered Human Risk Management platform that helps organizations reduce risk through modern training, policy management, phishing simulations, and intelligent automation. Our goal is to help companies build compliance programs that are effective, measurable, and built for the way people work today.

More than 6,000 organizations, including Shake Shack, WeightWatchers, Sephora, Jiffy Lube, and Y Combinator, trust EasyLlama. We're proudly bootstrapped, profitable, and recognized on the Inc. 5000 list, with a 96% G2 rating and industry-leading NPS and CSAT scores. We move quickly, value ownership and collaboration, and believe the best ideas come from people who are excited to solve meaningful problems and make a real impact.

Our CORE values

DRIVE is how we work at EasyLlama. Weʼre Doers, Resourceful,
Impactful, Valued Partners, & Excellence-Focused.

• We are Doers. We proactively make things happen.

• We are Resourceful. We treat time, money, and energy as valuable.

• We are Impactful. We prioritize what matters.

• We are Valued Partners. We put customers & teammates first.

• We are Excellence-Obsessed. We always deliver excellent work.

From CEO to newest hire, DRIVE asks us to take ownership, solve
problems, prioritize what matters, support teammates, and deliver high-
quality work.

When we live these values, our product choices, customer interactions,
hiring, and promotions all help us live out our mission: to build safer and
more productive workplaces.

We’re hiring a Technical Support Specialist to own escalated, technically complex customer issues.

You’ll step in when problems go beyond standard support—owning investigations, troubleshooting integrations, and working cross-functionally to drive resolution. You’ll act as the bridge between Customer Success, Product, and Engineering, ensuring issues are clearly understood and efficiently resolved.

This role also supports pre-sales and onboarding, helping prospects and new customers navigate technical questions and set up for success.

This is a high-ownership IC role that requires strong technical problem-solving, clear communication, and the ability to operate across teams.

• Own and resolve escalated technical support issues, including integrations and complex product behavior

• Troubleshoot across systems, APIs, and third-party tools to identify root causes

• Act as a liaison between Support, Product, and Engineering on technical issues

• Clearly document issues, reproduce bugs, and communicate context to internal teams

• Ensure timely resolution and consistent follow-through on all escalations

• Support pre-sales conversations by answering technical questions from prospects

• Partner with Customer Success during onboarding to guide customers through technical setup

• Identify recurring technical issues and drive improvements to:

  • Documentation and help center content

  • Internal troubleshooting workflows

  • Product feedback loops

• Maintain clean, accurate records in support and CRM systems

• Answer technical questions and provide recommendations to internal teams

• 3–5 years in Technical Support, Solutions Engineering, or similar role

• Strong troubleshooting skills across integrations, APIs, and SaaS tools

• Ability to clearly communicate technical concepts to both technical and non-technical audiences

• Highly organized with strong attention to detail

• Comfortable working cross-functionally with Product and Engineering teams

• Proactive and resourceful — you take ownership of problems and drive them to resolution

• Experience working with SAML, SCIM, SFTP, webhooks, or integration platforms

• Familiarity with tools like Zoom, Slack, HubSpot, Linear, or similar SaaS ecosystems

• Experience in a B2B SaaS environment

• Experience using AI tools

• Exposure to pre-sales or onboarding support

• Escalated technical issues are resolved quickly and thoroughly

• Clear communication between Support, Product, and Engineering

• Reduced repeat issues through improved documentation and feedback loops

• Prospects and new customers feel confident in technical setup and capabilities

This role ensures that complex technical issues don’t slow down customers or the business. You’ll play a critical part in resolving high-impact problems, improving the product through feedback, and supporting customers at key moments—from evaluation to onboarding.
What to Expect

The interview process at EasyLlama takes about 3-4 weeks and will include cross-functional stakeholders of the role. Here's what the interview process looks like:

• Recruiter Screen

• Hiring Manager Interview

• Peer Interview

• Executive Interview

• Reference Checks

How We'll Take Care of You

• $75K – $95K Base salary + Bonus potential

• Flexible, fully remote environment

• Competitive employer-sponsored health insurances

• 401(k) + company matching

• Professional development reimbursements

• Quarterly remote work stipend

*The EasyLlama herd is fully remote, with employees distributed across the US. We are currently hiring in the following approved* states:
AR - Arkansas
CA - California
CO - Colorado
CT - Connecticut
FL - Florida
IL - Illinois
LA - Louisiana
MA - Massachusetts
MI-Michigan
MN - Minnesota
NJ - New Jersey
NY - New York
NC - North Carolina
OH - Ohio
OR- Oregon
PA - Pennsylvania
TN - Tennessee
TX - Texas
VA - Virginia
WA - Washington
WI - Wisconsin

*EasyLlama reserves the right to change the list of approved states at anytime.

*To ensure the best employee experience, we offer competitive compensation packages, comprehensive benefits, an annual wellness stipend, PTO, 401k with company matching, and monthly team events to nurture connection!

At EasyLlama, we strive to walk the walk. We are helping make workplaces all over the globe safer and more inclusive, including our own. We honor employees and candidates from all walks of life and all experiences, regardless of race, ethnicity, veteran status, disability, sexual orientation, gender identity or religion.
*Applies to full time (W2) employees.