Kara Seymour: scaling your career on vibe, velocity, and calculated bets

Welcome to Escalations, a series where I’ll be sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

Introduction: the starting point

Kara Seymour’s career didn’t begin with product dashboards or ticket queues. After studying sports medicine and working as an EMT, she took a “benefits-first” job on the phones at Blue Cross Blue Shield in rural Illinois. Very quickly, she found herself training peers and growing a claims team from 50 to 450 people—work that lit up her builder’s instinct.

The growth path

Kara’s résumé is a series of intentional leaps. She left the safety of Blue Cross for a five-person startup (Crowdcast) when boredom outweighed security. Two colleagues then convinced her to join Hopin as employee #12, where she scaled global 24/7 support in sixteen months. After a brief detour in mar-tech—“busy work that drained me”—she found her sweet spot at Forma, blending her healthcare roots with SaaS speed.

Along the way she faced two recurring hurdles. First, skill gaps: teaching herself workforce-management math so thoroughly that Finance now uses her spreadsheet. Second, perception: turning support from scapegoat to strategic partner by setting clear boundaries (“log a Jira ticket before you ping me”).

Implementing this in your own career

• Track the moment you feel restless; it signals readiness for a bigger stage.

• Pick one high-leverage “utility” skill—WFM, SQL, QA—and master it until you can explain it at a whiteboard.

• Write a one-pager explaining why your function exists and share it; clarity builds influence.

Breaking through: lessons & key decisions

1. Hire—or be—the vibe fit first
Kara believes culture-add beats résumé lines. At Hopin she hired a former barista who could “diffuse tension with a joke.” Within six months he owned chat QA and built the macros library that slashed handle time.

How You Can Apply It

• Spotlight your soft strengths—curiosity, composure—early in interviews.

• Draft a 90-day learning plan for any hard gap before day 1.

2. Draw boundaries to raise your stock
When she arrived at Forma, support was the default dumping ground. Kara introduced a two-step gate: before pinging support, colleagues had to (1) file a Jira ticket and (2) include reproduction steps or data. The friction forced upstream ownership and cut random Slack pings by 38 % in a quarter.

How You Can Apply It

• Block focus hours on your calendar (and defend them).

• Convert repeat questions into templates or macros to curb interruptions.

3. Speak the language of dollars and head-count
Scaling 24/7 coverage across 24 countries required budget credibility. Kara built a Google-Sheets model with arrival patterns, shrinkage, and cost per interval. After three straight quarters forecasting within ±2 FTE, Finance began using her template.

How You Can Apply It

• Learn a basic forecasting or reporting tool relevant to your lane.

• Translate wins into cost saved or revenue protected.

4. Turn slow weeks into résumé gold
Kara invented “Seasons of Growth,” a programme that transforms low-volume months into career sprints. Each rep proposes a cross-functional project—like auditing onboarding emails or localising KB articles—then ships it before volume spikes again. One audit removed 17 friction points and cut new-account churn by 4 %. Demo days give contributors exec exposure and bullet-worthy achievements.

How You Can Apply It

• Identify a predictable lull in your calendar.

• Pitch a scoped project with a clear metric and a two-page recap.

5. Treat every conversation as market research
After the Hopin layoff, Kara accepted every recruiter call for three months. Beyond openings, she harvested salary bands, tooling trends, and interview questions she now shares with her team.

How You Can Apply It

• Book one curiosity call each month: recruiter, vendor, or peer.

• Keep a running doc of pay ranges, pain points, and standout questions.

Actionable takeaways

• Chase cultural fit, then stack skills

  • Fit accelerates trust and collaboration.

  • A 90-day upskill plan bridges hard gaps quickly.

• Guard your focus to deliver deeper work

  • Scheduled focus blocks increase output quality.

  • Clear boundaries teach colleagues to self-serve first.

• Quantify your impact

  • Framing results in dollars makes leaders listen.

  • Data fluency unlocks cross-functional invitations.

• Exploit quiet seasons intentionally

  • Side projects showcase initiative beyond core duties.

  • Finished projects create easy résumé bullets and talking points.

• Network like an R&D lab

  • Conversations reveal hidden market and salary insights.

  • Logging takeaways turns casual chats into strategic assets.

Where they are now & final words of advice

Kara is Senior Director of Global Support at Forma, proving frontline roots can power executive altitude. Next on her five-year roadmap: pivot into product so support’s voice shapes features from day one.

Do you have a story to tell or insights to share? Consider having a conversation with me so I can share something like this about you!