Sales DirectorNow
Federato
The AI-native core system for commercial P&C insurance. Changing the way insurance work gets done.
I win complex enterprise deals, and I help teams win more of them.
I'm James O'Connor, Sales Director at Federato, the AI-native core system for commercial P&C insurance. For the last 11 years, I've worked at high-growth startups from Series A to E and closed deals from mid-market to the largest enterprise accounts.
11years in enterprise closing roles
$23.7Mclosed-won across 5 startups
5xPresident's Club
5x#1 AE in company
About
Hi, I’m James.
I’ve been the founding SDR on a team, the founding AE of a mid-market team to bring the company downmarket, a sales manager leading four AEs across the West region, and a strategic AE closing the company’s largest deals of the year.
I’ve spent my career in sales, with the last 11 years in enterprise closing roles at high-growth startups: AppDirect, Talkdesk, Vivun, Instruqt, and now Federato, the AI-native core system for commercial P&C insurance.
Across five startups, from Series A to Series E, I’ve closed $23.7M in revenue, made President’s Club five times, and finished as the #1 AE in the company five times.
What ties it together is how I sell: a deep understanding of our technology and differentiators, executive presence, quarterbacking complex governance and multi-threading strategies, and always asking, “Why might we lose?”
[James] is competitive in a way that brings out the best in his peers; always eager to help, support, and establish processes that drive 10X value to an organization.
Tom Rice, Chief Revenue Officer
- Every account gets an org chart.Deal strategy is meaningless without understanding reporting structures and power bases.
- Team selling, always.It takes a village. Presales, product, success, delivery, and leadership all have a role to play.
- Outcomes over capabilities.Customers buy for business outcomes, and capabilities enable those outcomes.
- AI-native is a must.Building agents, plugins, and skills lets me 10x myself and the team around me.
Experience
A decade-plus, five startups.
Sabbatical
Seven months to plan a move to Austin from Bend, OR, think deeply about my career, dive extensively into AI, and accumulate over 50 days at Mt. Bachelor during a record-breaking season.
Strategic Account Executive
Instruqt
#1 AE in Q3. Migrated a book of 15 existing accounts onto a new prepaid consumption model while growing the book 21%.
Sabbatical
Seven months off after a 14-year run building my sales career, spent with family and friends, traveling, and learning.
Strategic Account Executive
Vivun
#1 AE in FY22 (181% of quota) and FY23. AE of the Year FY22. Deal of the Year FY22 and FY23.
Sales Manager, West
AppDirect
Led four AEs on a $10M TCV new-business quota. #1 team in FY20 and the largest deal of the year ($5.4M TCV).
Enterprise Account Executive
AppDirect
#2 AE in FY19 (145% of quota). 105% of FY18 quota. Deal of the Year FY19.
Mid-Market Account Executive
Talkdesk
#2 AE on the newly formed mid-market team. Founded a Lunch & Learn program to drive pipeline with Salesforce.
Mid-Market Account Executive
AppDirect
Founding AE on the newly formed mid-market team. Co-developed the playbook and pricing strategy. Rookie of the Year FY15. #1 AE in FY16-H1.
Sales Development Rep
AppDirect
Founding SDR for AppDirect. Built the inbound and outbound process, implemented tooling, and generated $8M+ ARR in pipeline.
Career wins
Deals I'm proudest of.
Customers are anonymized. The figures are real, and I'm happy to talk through any of them in detail.
F50 Telco · AppDirect
Digital commerce platform to launch new revenue stream
F50 Telco wanted to bundle value-added cloud services with its core connectivity and sell through an omnichannel experience to its business customers.
$5.4MTCV
$1.6MARR
$3B ERP ISV · AppDirect
Digital commerce platform for developer ecosystem
$2.7MTCV
Regional Telco · AppDirect
Launch VAS cloud revenue stream for SMBs
$1.9MTCV
T1 Carrier · Federato
AI-native core suite (policy, billing, claims) for new LOB
$4.1MTCV
$3B CX ISV · Vivun
Presales platform to support cloud GTM transformation
$525KARR · Largest deal in company history
Value selling · Vivun
A value case model that won the year's biggest deal
Later adopted by the broader sales team.
FY23Largest deal of the year
Contact
Let's talk.
- Recruiters and hiring managersI'm always glad to have a conversation, even if the timing isn't right yet.
- Everyone elseSay hello. I enjoy meeting people who are building things – especially if you're in Austin.