About the Position
As the Revenue Operations System Administrator at WatchGuard, you will be the operational backbone of our sales enablement tech stack — ensuring that the tools our global sales team relies on every day are running smoothly, configured correctly, and fully adopted. This role sits at the intersection of sales, marketing, and operations, and has a direct impact on the productivity and effectiveness of our sales organization across the US, LATAM, EMEA, and APJ.
You will own the day-to-day administration, user management, and troubleshooting for our core sales enablement platforms: Outreach, Kaia, ChiliCal, and Sendoso. You will be the go-to resource for sales reps who need support, configuration changes, or guidance on how to get the most out of these tools. You will also serve as a backup resource for the field marketing team on Sendoso gifting needs.
This role reports to the Sales Enablement Manager and is part of the broader Revenue Marketing team — a cross-functional, tightly aligned organization that includes sales enablement, demand generation, marketing operations, and digital environments.
A Day in the Life
No two days will be exactly the same in this role. You might start your morning triaging a support ticket from a sales rep who can’t access their Outreach sequences, then spend time building and optimizing a new sequence for an upcoming go-to-market play. Your afternoon might involve updating Kaia coaching cards to reflect a recent product launch, then fielding a request from a Channel Development Manager who needs a custom ChiliCal link set up for an upcoming partner outreach effort.
You’ll regularly coordinate with the Sales Enablement Manager on prioritization and platform roadmap needs, and you’ll work closely with sales reps and leaders globally to make sure every tool is configured to support the current selling motion. Given the global nature of WatchGuard’s sales team, some flexibility in your schedule to support team members in different time zones will be important.
Within One Month, You Will…
• Complete an audit of current user setups, permissions, and configurations across Outreach, Kaia, ChiliCal, and Sendoso
• Get familiar with the current sequence library in Outreach and understand the go-to-market plays they support
• Meet key stakeholders across global sales, sales enablement, marketing operations, and field marketing
• Handle your first round of user management requests and troubleshooting tickets independently
Within Three Months, You Will…
• Fully own user provisioning, deprovisioning, and access management for all four platforms
• Build and launch your first optimized Outreach sequence in support of an active sales play
• Establish a regular cadence for Kaia playlist and coaching card reviews to keep content current and relevant
• Define and document standard operating procedures for the most common admin requests and troubleshooting scenarios
Within Six Months, You Will…
• Deliver regular Outreach reporting to sales leadership, including sequence performance, rep activity, and adoption metrics
• Have a fully documented, optimized process for all platform admin functions across Outreach, Kaia, ChiliCal, and Sendoso
• Proactively identify and implement improvements to platform configurations that drive sales productivity
• Serve as a trusted resource for both the sales enablement and field marketing teams on all platform-related needs
Responsibilities
Outreach Administration & Optimization
• Own all user management in Outreach, including provisioning, deprovisioning, role assignments, and permissions for the global sales team across US, LATAM, EMEA, and APJ
• Build, manage, and optimize sales sequences in alignment with active go-to-market plays, ensuring sequences are current, accurate, and effective
• Serve as the primary point of contact for Outreach troubleshooting and support requests from sales reps and leaders
• Own Outreach reporting — pulling and presenting performance data on sequence activity, rep engagement, and platform adoption to the Sales Enablement Manager and sales leadership
• Monitor platform health and proactively identify configuration issues, underperforming sequences, or adoption gaps
Kaia Administration & Content Management
• Own the creation and management of Kaia playlists, coaching cards, and topic cards, ensuring all content reflects the latest product messaging, sales plays, and enablement priorities
• Regularly review and update Kaia content in partnership with the Sales Enablement Manager and product marketing to keep it accurate and impactful
• Manage user access and permissions in Kaia for the global sales team
• Troubleshoot Kaia issues and respond to support requests from reps and managers
ChiliCal Administration & Calendar Management
• Own the administration and user management of ChiliCal for the global sales team
• Create and manage calendar links as requested by sales reps, including standard links and custom configurations for specific outreach needs
• Troubleshoot scheduling issues, broken links, and integration errors in ChiliCal
• Maintain documentation of link types and configurations to support consistent and scalable setup for new team members
Sendoso Administration & Support
• Own the back-end user management and permissions for Sendoso across the global sales team
• Assist sales reps with their Sendoso gifting links, direct mail sends, and troubleshooting of platform issues
• Serve as a backup resource for the field marketing team on Sendoso campaign execution and support needs as required
• Stay current on Sendoso features and best practices to help drive adoption and effective use by the sales team
Cross-Functional Collaboration & Process
• Partner closely with the Sales Enablement Manager on platform roadmap priorities, tool improvements, and enablement alignment
• Coordinate with sales operations and marketing operations on integrations, data flow, and CRM-connected platform configurations
• Develop and maintain documentation for all platform admin processes, standard operating procedures, and user guides
• Proactively identify opportunities to automate or streamline admin workflows to improve efficiency and scale
Skills and Qualifications
• 1–3 years of experience in sales operations, revenue operations, marketing operations, or a sales enablement support role
• Hands-on experience with Outreach or a similar sales engagement platform; experience building and managing sequences is a plus
• Familiarity with Kaia, ChiliCal, Sendoso, or similar sales enablement and gifting tools
• Comfort working with CRM systems; Salesforce experience preferred
• Strong attention to detail and a low tolerance for broken processes or bad data
• A genuine interest in helping salespeople work more efficiently and effectively
• Ability to manage multiple requests simultaneously and prioritize based on urgency and business impact
• Strong written and verbal communication skills, with the ability to communicate clearly with both technical and non-technical stakeholders
• Comfortable working across time zones to support a global sales team in US, LATAM, EMEA, and APJ
• Self-motivated, highly organized, and a natural problem-solver
• Bachelor’s degree or equivalent work experience