Ally Kavanagh has sold radio ads in Boston and enterprise software in London. On episode seven of Sales Rewritten, HubSpot's Lead Enablement Partner for EMEA shares what 15 years in sales has taught her about resilience, EMEA selling and enablement.
Ally Kavanagh's first sales job came with a phone book, a laptop and the whole of Massachusetts as her territory.
More than 15 years later, she helps around 250 HubSpot sellers across EMEA get better at their craft.
In episode seven of Sales Rewritten, she tells host Alex Wood why the hardest deals are the most rewarding, why Europe is a tougher market than the US, and how she went from doubting sales enablement to leading it.
Ally fell into sales after college, starting out selling radio advertising for CBS in Boston.
In 2012 she joined HubSpot as a BDR, when the company had around 340 employees and a daily leaderboard that showed everyone's calls, emails and meetings.
Competition was part of the culture, and Ally loved it.
"If I really believed that I could help someone solve a problem or I could help someone achieve a goal, that was really motivating to me. And knowing that I'd earned it was really important as well. Some of the deals that just come easy, they're not satisfying as the ones that you really put in a [graft] for."
One of those deals was with a small couple-run business that had qualified itself out on price.
Ally built the business case anyway and won them over. The owner later emailed HubSpot's CEO to thank her, and the leadership team signed a printed copy that she still keeps framed.
In 2018, Ally moved to London to become HubSpot's first salesperson on the ground.
She quickly learned that British idioms and expressions will take some getting used to.
For example, when one of her champions told her a business case was "not ideal", she assumed they were nearly there.
They weren't.
"I think selling in Europe is way harder... The buyers are much more skeptical. A ton more scrutiny on the types of investments that they make. Most decisions are made by committee."
Her advice for anyone crossing the Atlantic is to be self-aware, own what you don't know, and do the work upfront to earn a buyer's trust.
Buying committees mean more people to reach. See how data enrichment helps you find and contact every stakeholder, not just your champion.
At Salesloft, Ally moved into bigger, more complex deals.
She says every strong enterprise deal needs a senior champion willing to push for change and a business problem validated by multiple stakeholders.
She learned to love MEDDPICC because it gives everyone a common language and keeps everyone honest about their pipeline.
She's also a stickler for the basics, like sending an agenda before every meeting and following up fast.
"Same day. And if it's not within like a couple of hours, I would send an email that says, 'Hey, thanks for the call. I've got everything. I've got a couple of meetings coming up. I promised you this, this, and this. I'm gonna get you this by 9am tomorrow.' It's just a little thing."
Not every signal means what it seems. Ally warns that a new senior hire isn't always a green light. Learn to read B2B buying signals with more confidence.
Ally admits she spent years as the seller who switched her camera off during enablement sessions.
"I've been that seller who didn't think it was important, who didn't buy into my sales enablement team, didn't think they had credibility, didn't think that they knew my job, didn't think that they knew anything to teach me."
Now back at HubSpot, she is determined to do enablement well.
Much of that work is about AI, using it to take admin off sellers' plates while keeping everything inside the CRM.
She says she doesn't see AI replacing sellers in the enterprise, where buyers still want a trusted human partner.
There is plenty more in the episode, including the mock sales call that terrified her at college, what a typical week in field enablement looks like, and how she resets after a bad day.
Ally Kavanagh is Lead Enablement Partner for EMEA at HubSpot. She has sold in Boston, New York and London, including enterprise roles at Conductor and Salesloft. Find her on LinkedIn.
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