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James O'Connor
VP of Sales

James O'Connor

James drives our sales strategy, building relationships with businesses and developing our sales playbook.

Based in

Boston, MA

On the masthead since

November 2019

The beat

B2B Sales, Negotiation, CRM Management, Pipeline Development, Demos

Off the clock

Golf, Boston Sports, Cooking

About James

Hey! I’m James.

I’ve been in B2B sales for over 8 years, and what I love most is helping businesses find solutions that genuinely make their lives easier. I’m not about the hard sell - I believe in understanding what customers actually need and being honest about whether we’re the right fit.

Before joining the team, I was at a SaaS company in the HR tech space where I consistently exceeded quota and helped train new sales reps. When I saw the opportunity to join an early-stage startup and build a sales function from the ground up, I jumped at it.

I’ve helped develop our sales playbook, demo scripts, and qualification criteria. I work closely with our marketing and product teams to make sure we’re telling a consistent story and learning from every customer interaction.

Outside of work, I’m a die-hard Boston sports fan (go Celtics!) and spend my weekends on the golf course trying to break 80. I also love to cook - my Sunday sauce recipe has been passed down for three generations.

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