Hosted by: Jody Geiger

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Salesforce’s Jessa Jennings is the Vice President of Sales Performance Management for Commercial & Enterprise in North America. Throughout her more than 14 year career with Salesforce, she’s held many titles including the first female regional vice president at Salesforce Canada. Here are three takeaways from her conversation with Jody.

1️⃣ Women leading women to lead 1️⃣

It was the first time in her career she was the only woman in the room. A male-dominated industry (sales) selling into a male-dominated vertical (manufacturing). But instead of being intimidated by being the only one, it motivated her.

Because when you’re the ‘only one’ —youngest, oldest, female — it gives you an opportunity to shine. And that’s exactly what she did at a pitch competition back in 2009.

She made it to the final three and gave her presentation in front of a top sales leader, who is now a member of the executive leadership team at Salesforce.

The pitch went so well she not only won the competition, that sales leader said they would hire her to move up to an AE role from SDR on the spot.

“I really felt like I’d made it at that point. It gave me the confidence. I don’t even think he knows how impactful that was.”

Leaders sometimes don’t realize how the right feedback at the right time can change the entire trajectory of someone else’s career. But Jessa does realize it. And she makes sure to take any opportunity she can to pay it forward — especially to women.

” I think about that when I’m coaching my reps. I have a lot of conversations with women in our organization that are going on their first mat leave and trying to manage their career through that.”

She puts those soon-to-be mamas at ease by instilling confidence in them. Letting them know their brand is strong enough to take a year off and come back without falling behind.

Both Jessa and Jody take leading other women very seriously. They know what it’s like to have the odds stacked against them, and remember the people in their lives who supported them when they need it most.

And now they get to be the leaders who instil confidence in the next generation of female leaders.

Watch the Season 2 premiere of Winning as Women with Loopio’s Sr. Director of Revenue Enablement Steph White!

2️⃣ Financial and business acumen are key to selling into the C-suite and CFOs 2️⃣

Selling to CFOs in some ways is no different than selling to any other persona. Getting personal, understanding their pains and positioning your solution as the right one to solve them. The difference with CFOs though is that their pains — and solutions for those pains — are highly complex.

That’s why Jessa says sellers need to develop both financial and business acumen in order to properly diagnose and cure what ails them. That involves drilling down into every business unit your tool or tech could solve for, understanding what’s costing them the most time and money and presenting a solution.

“If you can’t say this is what it’s costing you today, then I don’t really think you’ve earned the right to be in front of the CFO as of yet.”

With CFOs, sellers need to understand their prospect’s business at a deeper level of specificity than with other kinds of personas. It’s still about getting personal. But understanding what’s personal to a CFO demands sharp knowledge of the business environment more broadly, and the internal stressors at play.

Get as much information as you can on the company, through publicly available sources and your own internal intel, and push yourself to be always learning and understanding the business and financial paradigms of your prospect.

Watch host Jody Geiger talk about life as a revenue enabler on the Competitive Enablement Show

3️⃣ It all starts with effective discovery 3️⃣

Pipeline often dies at stage two of the sales cycle. That stage for Jessa is the discovery phase. Especially when budgets are tight and you’re having to sell into senior leaders like the CFO, uncovering the buyer pains is absolutely vital.

But it’s not enough to simply unearth the pains, and for your internal team to be clear on them. You need to make sure your prospect agrees on the pains, and see you as the right partner and solution to address the pain.

“I noticed in our sales cycles over the years sometimes we do all this discovery, but we’re leaving that call and our prospect might not actually see the pain. We assume they see it. But they don’t.”

As Jessa puts it, “You have to marinate in it”. Sit there on the call or in the room, and let the silence speak volumes.

Then, at the right opportunity, start building that all-important partnership with your champion who will help make your solution a success.

You can only get there with effective discovery.