Riskonnect
Riskonnect is the market-leading integrated risk-management platform that connects strategic, operational, and cyber risks in one dashboard.
AUDIENCE: Sales and marketing leadership (150)
LOCATION: Sales-kickoff on a Royal Carribean cruise departing Fort Lauderdale, Florida and traveling through the Bahamas
CHALLENGE: With aggressive growth targets and a new go-to-market playbook, Riskonnect wanted a keynote that would galvanize quota-carrying teams and rally marketing behind a unified message of ownership and adaptability.
CARA BROOKINS’ SOLUTION:
45-minute keynote: “Be Part of the Crew” tailored to a nautical SKO theme (+ interactive Q&A)
Collaborated with Amy Hawkins on pre-cruise content call
Onboard meet-and-greet sessions for personalized team engagement
Continued networking and activities with the team throughout the 5-day cruise
Riskonnect’s annual SKO set sail—literally—on a multi-day cruise, transforming conference rooms into ocean-view brainstorming hubs. To anchor day one, organizers chose Cara Brookins, whose seafaring-themed keynote “Be Part of the Crew” mapped her family’s home-building odyssey onto the high-pressure world of enterprise SaaS sales.
Cara challenged reps to treat each customer story like a structural blueprint: ask deeper questions, reinforce trust, and anticipate storms. Cara referenced her own background in technology with 20 years as a software developer, combined with stories of her crew of four children as together they built their own two-story house from the ground up. She then coached marketing leaders on building “seaworthy” narratives that keep prospects on board through complex buying journeys.
In addition to her performance, Cara personalized team engagement by attended onboard meet-and-greet sessions, dinner events, and additional on-ship and off-ship activities with the team.
Post-event feedback cited an uptick in seller confidence scores, and pipeline commentary referenced Cara’s “Captain’s Checklist” for navigating objections, proof that her motivational approach translated directly into sales execution.
