How to Go From BDR to Enterprise AE in 3.5 Years | Jolie Stern (Gong)

Carter (00:01.417)
Hey Jolie, give the people a quick intro. Who are you and what do you do?

Jolie Stern (00:05.378)
Hi everyone, my name is Jolie Stern. I grew up in Connecticut, spent eight years in New York City postgrad, and now I'm based in Miami. I've spent my entire career in sales, starting at a full service digital marketing agency in New York City, eventually moving over to Slack and then Salesforce once we got acquired, and now I am at Gong.

Carter (00:29.899)
Okay, so you started at Slack as a B D R well you started at Slack as a B D R in less than five years there, you're an enterprise AE and then an R V P. How did you move up so fast? Was it results, taking on big problems, navigating a bunch of politics? Like how yeah, how did you do that?

Jolie Stern (00:35.075)
Mm-hmm.

Jolie Stern (00:48.024)
Yeah, great question. I am so grateful for all the opportunities I've had. I think it really comes down to two pieces. One is internal networking. I think like never be afraid to introduce yourself to a leader. And if you do have a leader that you want to introduce yourself to, come prepared with a question, something that can make the encounter memorable. I think the goal for me was always building a strong brand for myself. That's

Really important at a big company like Salesforce. The goal is to build as many relationships as you can and

Of course, execute on the role as well, so that if there is a job opening, you're the first person that comes to mind for that leader. And I think the other thing to note is that building a network can help you in more ways than just your next promotion. You can build a community of mentors who you can give a call when you need deal strategy, people who are more experienced and that you can learn from, or you can build relationships in deal desk or legal.

That you have friends in the right places when your deal is starting to get a little bit chaotic. And these relationships can give you opportunities like being chosen for leadership committees, AI committees. I think the other piece, and this isn't for everyone, but a big value of mine has always been making an impact, both on the dashboard, my quota attainment, but also off the dashboard. And I say this isn't for everyone because if you're not

Number one goal is to make money in sales, focus on those client activities, put your energy towards the money. But if you have goals to be in leadership, be that person who joins a team and immediately is raising the bar for what excellence looks like. And don't just be that model of what good looks like, but share what you're doing with everyone. Have those processes that can scale, that are documented. And as you become someone that you're

Jolie Stern (02:56.736)
leader can really count on. Don't raise problems to leadership without a solution on how you can actually solve it. And that's where you start to actually create meaningful change in an organization and real impact that I think people remember.

Carter (03:14.727)
You've been at Gong for a few months now. When you join a new company as an experienced seller, what are the first things you try out? And then is there a still a big learning curve or do most of the skills transfer pretty well?

Jolie Stern (03:27.363)
Yeah.

I mean, there's always gonna be a learning curve, and change is always a little bit scary. You have to learn a new product, new talk tracks, internal politics, but the sales foundation is pretty easy to transfer. I chose gong because I wanted to sell a product that I was gonna live and breathe in every single day. Something that I actually get to touch, something that I could create an emotional sales cycle around, similar to my time.

At Slack. That's also a product that I really believe in and I got to touch every day, and I still get to use it. And I think that that made it a lot easier to ramp quickly because you feel comfortable speaking about the product and you feel comfortable demoing because you're actually using it. I think the most important thing for starting over and really hitting the ground running is one getting as organized as possible. Something I like to do is create a Slack channel for myself.

Resources and when there's a ton of noise, whenever I see something important, I just forward it to that channel. It gives me a really easy place to search and stay on top of great items. I also think, you know, the classic owning your book of business, tiering your accounts quickly, building those points of views, and starting fast on anything that's warm, whether it's a renewal, a lost opportunity, a connection. And lastly, I'm very spoiled.

to have a tool like Gong where I can watch exactly what the top performers are doing and learn and try to implement that into my process.

Carter (05:07.379)
Did you use Gong at slack?

Jolie Stern (05:09.12)
I actually didn't. I wish I did. I was a frontline sales leader for a bit of time, like you mentioned. And there were moments where my team had 40 opportunities per rep in one month. It was pretty chaotic. So a tool like Gong really helps take some of that load off of a manager or a seller to really know what's happening in a deal.

Carter (05:33.599)
And tell me more about this resources tab or this Slack channel. What do you mean by that? Like what type of stuff do you put in there?

Jolie Stern (05:38.284)
Yeah. There's a lot of ways to use Slack to be creative. When I was at Slack, my resource channel was actually public. So I would post resources that I made, whether it was a deck, an executive summary, a call that went really well. So that whoever wanted to join was essentially like subscribing to my

Page of resources. At Gong, I did keep the channel private for now because I'm new and I'm learning. But the reason it's so nice is when you forward everything into a Slack channel, it gives you a much smaller base to search. So you can just search that channel if you know something is in there and find what you need a lot faster.

Carter (06:22.685)
You've been selling into the financial service or into financial services for the last five years and with the move to Gong, you're still staying in that vertical or in that industry. How has compounding helped your career? And did you do that on purpose? Like would you recommend AEs build their career in one vertical or jump around a lot? Because I know you started out not in that in that vertical.

Jolie Stern (06:44.846)
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My first job was pretty industry agnostic. And honestly, I don't think there's anything negative about jumping around. I've watched some of my favorite leaders at Slack and Salesforce pivot between different verticals. But for me, this was a hundred percent an intentional choice. I wanted to become a master in my space. I think it's provided me with opportunities that I wouldn't have had otherwise. Financial services firms, for the most part.

Have clear processes, they have clear budget cycles, and they are sometimes the laggers when it comes to chain change, excuse me, but in my opinion, it just means it's a less saturated market when you're selling technology. You can learn to

If you can learn to take your company's positioning, for example, Slack or Gong, a tool that traditionally is marketed to an a tech company or a traditional sales company, if you can speak the language of a wealth and asset management firm or a bank and a credit union or an insurance firm and take that positioning, use that business acumen to deliver value. I think there's a lot of opportunity to make money. That's what I found.

At Slack, and I'm definitely finding that at Gong. We have such an incredible financial services and industries team with really great industry-specific resources. And again, it's a lot of white space. We have incredible titles. The financial services firms are adopting quickly, but it's not like selling into high-tech where these accounts have been called over and over again year after year.

Carter (08:33.887)
Right. You have said that financial services is a space that's traditionally slow to adopt new tech. When you're selling to people who've been doing the same things for a long time, how do you get them to move?

Jolie Stern (08:42.243)
Mm-hmm.

Jolie Stern (08:48.044)
Yeah, I think, you know, change management and just getting people to move, it is a challenge. And I think first and foremost, you need to build as much trust and as much, you know.

As many strong relationships as possible. You have to multi thread. You can't put all your eggs in one basket with one person. You should lean on proof points, customer references, and stories. And then, you know, this isn't groundbreaking, but face in the place, get on site, meet them in person. That's the number one way to build trust. People don't ghost you as easily when you have that face to face interaction. I also am a big fan of bringing my

Leadership in as early as possible, even if it's just a no-ask email to leadership saying, Hey, you know, I I'm really interested in this partnership. I'm here to support you if you need anything. And then tackle those objections, you know, head on. if they're worried about change management, focus on it and make sure that you can get past that piece.

For me, like I never stop being curious in a deal cycle. And so there's always, you know, a different person you can speak to, a different pain point to uncover. And then something a leader at Gong shared with me is it's important to find your champion, but it's also important to find who isn't your champion. Who do you need to convince to get a deal cycle actually moving and make change actually happen?

Carter (10:27.167)
What percentage do most of your deals you do in person, or is it only for some?

Jolie Stern (10:31.918)
I

Try to get in person where appropriate. I do have some accounts that are in an office setting, some are more spread out. I think it's most meaningful when you can get in person for an actual presentation, whether it's a demo, a pricing call, but getting in someone's office, I've had moments. I visited a credit union at Salesforce and just by going to the office, I had a meeting with one individual, but I got to meet their CEO, their chief security officer, all these different individuals.

individuals that I wouldn't have interacted with otherwise.

Carter (11:06.943)
What are the biggest objections that come up in the late stages of an enterprise deal there? And how do you and what do you say to get around those?

Jolie Stern (11:14.284)
Yeah.

You know, I kind of mentioned lightly, but change management has never not come up in one of my deal cycles in financial services. It's easier to get around if you can tackle it early on. I think first is deep discovery and really understanding their pain points, tying that to true business outcomes and ROI so that you can ask them, you know, this is the cost of not changing and actually being able to quantify that.

I think, you know, again, showing those success stories, getting on site, but if you can also simplify the deal process for them, say, you know, this is what a traditional evaluation process looks like with similar firms, or even, you know, bucketing out the

approach. So like this is where we start phase one low impact. This is medium impact, high impact, and this is the track we're gonna go on, or even a seed and grow deal of let's start with this small group that's more res are less resistant to change, happier to adopt new tech and grow from there. I think the other largest objection that happens in financial services is security and compliance. It comes up also in every

single deal I have ever worked in financial services. This one is a bit trickier. Obviously bring in your subject matter experts early, your technical folks, multi-thread to infosec.

Jolie Stern (12:50.222)
And from a legal perspective, I'm a big fan of sending a zero dollar order form early on so that legal can start to see language and work through those processes without actually seeing a cost until like value is confirmed and you're at that stage. But honestly, if you can't meet their requirements, it's a sign to walk away. I personally would rather have a really strong relationship and circle back when our technology can meet their components.

Carter (13:12.981)
Mm-hmm.

Jolie Stern (13:20.016)
Compliance requirements rather than giving them false information and trying to get the deal done, even though I know we cannot provide what they need.

Carter (13:29.737)
makes sense. Do a lot of deals die out that way, or do you actually catch a lot of people down the line, like several months or even years into the future where they come back and you do end up doing a deal with

Jolie Stern (13:40.746)
It's a mix of both. I think at both companies I've been at, we have continuously innovated from a security and compliance standpoint. At Slack, you know, when I started at Slack, we didn't have native data loss prevention or, you know, some of the plans gate kept integration with SAML SSO, which has now changed and there's a lot more opportunities. So there is ways to, you know, circle back, re-engage that debt opportunity because

They were interested in the product, it was just a limitation from a compliance standpoint.

Carter (14:16.179)
A lot of companies are super hyped on AI right now. How do you tell the difference between a serious prospect and a tire kicker?

Jolie Stern (14:24.075)
Yeah.

I think first and foremost, educate yourself on AI. Know your own company's AI tools and offerings. Test out different tools yourself, whether it's Claude, Gemini, and understand enough about the history of AI and the nuances to be confident in a conversation with a prospect. Every company obviously is thinking about AI, but if you're working with a traditional finance firm, there is a lot.

Due diligence that has to take place. So I think understanding what AI tools are you already investing in. If it's only part of the Microsoft Suite, I might use that as an indicator of okay, maybe you haven't actually made an AI purchase. but understanding, you know, is there an AI Tiger team, an AI internal committee, AI policy that you guys have ironed out? I also like to use LinkedIn Sales Nav to search for AI titles.

Carter (15:20.757)
Mm-hmm.

Jolie Stern (15:25.322)
To see if there is someone within the company who has a role that's specific to Gen AI or AI in general. And then I think most important is grounding every single conversation around AI in a true business outcome. It's not just about productivity and time savings anymore. That's what every single company is offering. But

Show that differentiation if your pros prospect is serious about a certain KPI, whether it's increasing MPS scores or increasing conversion rates, tie that into your value narrative. But I think, you know, ask those hard questions, ask point blank, is this curiosity or is there actually an executive-sponsored AI initiative? Who is owning that? What KPIs are they accountable for? And if they can't answer those questions, it's probably

A conversation around interest and not actually a buying conversation. But I think to tie that together at the end of the day, AI doesn't change great selling. It's just the product category. So the fundamentals are the same. You have to understand the business problem. You have to quantify the impact, identify your champion, and build that urgency around the why now.

Carter (16:31.947)
Mm-hmm.

Carter (16:44.807)
Okay, well that makes a lot of sense. I think we got some good stuff here. I will end it here.

Jolie Stern (16:49.742)
Awesome.