Selling in a changing market is tough. So we went straight to an expert who makes it look easy: Krysten Conner. As a Sales Strategist at Usergems, she’s perfected her process. In this exclusive interview, she shares her playbook. You’ll learn the best way to end a demo call, her tips for multi-threading successfully, and how to develop a true champion. She also opens up about the biggest mistake of her career and what motivates her right before a sales call.
Who is Krysten Conner?
Krysten Conner is a sales strategist for UserGems with a track record of exceptional performance. But her path to the top of the sales world wasn't a straight line. Her unique background and hard-won experience are what make her insights so valuable for sellers today.
From History Teacher to Top Sales Performer
Before she was a sales leader, Krysten was a history teacher. She made a career change into tech sales and quickly became a top performer at some of the biggest names in the industry, including Salesforce, Tableau, and Outreach. Her journey shows that the skills of a great educator—clear communication, understanding people, and structuring information—are also the skills of a great seller. She didn't just change careers; she mastered a new one, proving that a non-traditional background can be a massive advantage in sales. Her experience gave her a front-row seat to what works in complex B2B sales cycles.
A Career Built on Real-World Experience
Krysten’s advice isn't academic. She spent over a decade in the field, closing major deals and learning how to succeed after facing her own early-career struggles. Her strategies are forged from 12 years of real-world experience, not just theory. She understands the daily grind of a sales rep because she’s lived it. This hands-on background is why her insights are so practical and actionable for sellers who are managing their own pipelines and need guidance on what to do next, right from the inbox where they spend their day.
Personal Performance: A 47.6% Win Rate
The proof is in the numbers. Throughout her sales career, Krysten maintained an incredible 47.6% win rate. This isn't just a good number; it's an elite level of performance that reflects a deep understanding of the sales process, from the first touch to the final close. When someone with that track record shares their playbook, it’s worth listening. That high win rate is the result of the same strategies she now shares with other sellers, focusing on precision, champion development, and flawless execution on every deal.
A Mission to Help Sellers Succeed Faster
After a long and successful career, Krysten’s focus has shifted. Her mission now is to help other sellers reach top performance much faster than the 10+ years it took her. She’s passionate about giving reps the frameworks and confidence they need to bypass years of trial and error. She believes that with the right guidance, sellers can shorten the learning curve dramatically. Modern tools with AI-powered workflows are designed to do just that—guide reps to the next best action so they can build winning habits from day one and spend more time solving customer problems.
Featured in The Sales Leader Series
Krysten’s expertise is widely recognized, making her a sought-after voice in the sales community. She was recently a featured guest on the SAAS Sales Podcast as part of their popular Sales Leader Series, a platform dedicated to sharing insights from the best in the business. In the episode, she dives deep into her three secrets for closing pipeline, offering tactical advice that reps can apply immediately. It’s more than just a conversation; it’s a masterclass in sales execution, covering everything from multi-threading to developing champions. For any seller looking to absorb practical, no-nonsense strategies from someone with a 47.6% win rate, this is a must-listen.
Krysten Conner on How to Sell in Any Market
The messaging is going to have to be around doing more with less, or doing more with the same, versus what sellers are more used to like ROI.
Also focusing more on retention than new logo: how do we upsell and expand into our existing customer base versus this kind of growth at all costs mentality, which we saw for the past couple of years?
And to that point, the third thing would be that how organizations are viewing things is now more in NRR, or net recurring revenue, rather than new ACB. Because the least expensive customer is the one you already have. And so just focusing on that. We sell to sales organizations, and that's what we're hearing the most focus on.
Running Discovery Calls That Create Urgency
Krysten’s advice is spot-on: urgency isn’t something you create out of thin air. It’s something you uncover. She notes, "To create urgency during discovery calls, it's essential to ask questions that uncover the buyer's pain points and the consequences of inaction." This isn't about pressure; it's about clarity. Your job is to connect the dots for the buyer between the problem they have and the real business impact it’s causing. Asking questions like, "What happens if this isn't solved in the next quarter?" or "How much time is your team losing to this each week?" helps them quantify the cost of doing nothing, making the decision to act much easier.
A great discovery call starts long before you dial in. Walking into a call unprepared means you’ll waste precious time on basic questions instead of showing up with insights that lead to better ones. This is where having the right tools makes a difference. For instance, Mixmax’s Meeting Copilot can automatically pull account intelligence and past call summaries into your pre-meeting brief. This allows you to skip the generic discovery and ask pointed questions that reveal deep-seated challenges. You can then help your buyer build a strong business case for change, together, turning a simple call into a pivotal moment for the deal.
Qualifying Deals Without Being Pushy
No one likes feeling interrogated, and your prospects are no exception. Krysten points out that effective qualification requires a delicate touch. "Qualifying deals effectively requires a balance between being assertive and respectful," she says. "Use open-ended questions to gauge interest and fit, allowing the buyer to express their needs without feeling pressured." This approach transforms a qualification call from a checklist of your requirements into a genuine conversation about their needs. It builds trust and helps you identify opportunities where you can truly add value, rather than just trying to force a fit where one doesn't exist.
Part of qualifying respectfully is making the entire process easier for the buyer. Every point of friction, no matter how small, can make a prospect feel pushed. Think about the classic, clunky email chain trying to find a meeting time. It’s a hassle for everyone. A simple way to reduce this friction is by putting the control in their hands. With Mixmax’s one-click scheduling, you can embed your availability directly in an email. The buyer simply clicks a time that works for them, and the event is booked. It’s a small change that makes a big difference in how the interaction feels.
Using Engagement Signals to Prioritize Your Pipeline
One of the best ways to qualify deals without being pushy is to let the prospect's actions guide your next steps. As Krysten says, "Monitoring engagement signals, such as email opens and meeting attendance, can help prioritize your pipeline." A prospect who opens your proposal three times in an hour is sending a clear signal of interest. A prospect who never clicks the link to your case study is sending a signal, too. These actions are data points that tell you where to focus your energy. By concentrating on leads who show genuine interest, you can invest your time where it will have the most impact.
This is where having clear visibility into engagement becomes critical. Mixmax provides real-time engagement signals directly within your Gmail inbox. You can see who opened your email, how many times they viewed your attachment, and when they clicked your link. This isn't just interesting data; it's your roadmap for what to do next. It tells you which prospects are hot and ready for a follow-up, and which ones are cold, allowing you to spend your day working on deals that are actually moving forward instead of chasing ghosts.
Preventing Deals From Ghosting
There’s nothing more frustrating than a promising deal that suddenly goes silent. According to Krysten, preventing this requires a proactive approach. "To prevent deals from ghosting, maintain regular communication and set clear expectations," she advises. This means every interaction should end with a clear next step that both parties have agreed to. She also adds that following up with "value-driven insights or relevant content can keep the conversation alive." The key is to ensure every touchpoint gives them something useful, reinforcing your role as a helpful resource, not just another salesperson "checking in."
Manually tracking follow-ups for every deal in your pipeline is nearly impossible. Important conversations inevitably fall through the cracks. This is where AI-powered workflows can be a lifesaver. With Mixmax, you can build personalized, multi-step outreach sequences that automatically deliver those value-driven follow-ups Krysten talks about. You can schedule emails with relevant case studies, helpful articles, or check-ins timed perfectly based on their engagement. It acts as your safety net, ensuring consistent communication and keeping your deals warm, even when you’re busy closing another.
The Right Way to End a Demo Call
So I have a three-part demo framework that works very well for very short discovery calls, and it's just simply to match their urgency.
So there are three and that script kind of goes like this:
"Rita, it's been great to talk with you today, people generally join these first calls for a couple of reasons. One is just they're kind of in an education mode, they're interested in new tools that are coming out on the market, they happen to see us and they're just interested in finding out what we do. Second is they have a major revenue or churn problem that they needed to solve six months ago, and they're wondering if we can help them with that. And then the third reason is they're looking at revenue, they're looking at churn, you know, it's an issue, they want to solve it in the next 12 to 18 months, but nothing is on fire. And so I'm just curious where you would put yourself on that scale? And if it's over here, and it's just education, it's 100% fine. I'm just asking because I never want to chase anything."
And then because we've given the buyer or the prospect a range and we're not asking them to write us an essay, right, it's multiple choice, they can pick where they are. And they're also free to tell us, you know, "I was just looking" and that's valuable for us and for them, because now they're not going to have to deal with a salesperson trying to follow up 20 times. They can say, "Yeah, shoot me an email every once in a while, but I just wanted to know what you do."
What is Sales Multi-Threading (and How to Do It Right)?
What we've found is that multi-threading by just asking for introductions rarely works. So something else to consider before that first meeting is what I call the three-by-three-by-three method. And that means three buying personas, three-step sequence, three-part follow-up.
So first of all, the three buying personas before that first call. You want to find three people with VP titles, from departments that are typically involved in buying what you sell. And then you want to put all three of those into a three-step sequence that starts four to seven days before that first call.
The first touch is you're just going to leave a thoughtful comment on something that they post on LinkedIn. The second touch is you're going to give them a LinkedIn connection request, and you're gonna mention the post that you saw. And then the third touch would be either an email or a LinkedIn message about the meeting that you have coming up with someone else from their company that says, you know, "Hey, Rita, your colleague scheduled a meeting with me. I thought you might be interested. The topic is tracking your past buyers' job changes and also lowering churn risk. Also, automatic multi-threading. Executives in your department aren't always involved, but sometimes they have specific OKRs that are relevant. Should I forward an invite? If not, that's fine, happy to keep you posted."
And then the three-part follow-up is, on the day that you have the meeting with their colleague, you're going to send them a very short three-bullet recap of that meeting. Also, on the day of the meeting, you're going to put them into a nurture sequence. It's usually something to do with thought leadership. Or if there are additional meetings on the calendar, reminding you to follow up with them and give them that recap.
And then a week later, you're gonna ghostwrite an email for your executives to send to the executive that you met with or the ones you've been contacting, because you want executives to start their own private channel of communication about your product.
How to Find and Develop a Sales Champion
I like to think about it as testing to see if they are a champion. And then once we've determined that they are, kind of developing them. I like to think about it as testing to try to determine if they are a champion in three ways–by asking them for three different things.
The first is by asking them for introductions to other people in their organization who are interested or have a stake in what you're selling. Not necessarily executives, but just an introduction to someone else on their team or in their org.
Second, I like to ask them for specific metrics. "You said your team wants to grow your pipeline?" Probably every sales team in the world would say that. "What kind of metrics are we talking about here? Are we talking about 8% growth? Do we need 18% growth? What are we talking about?"
And then the third is I like to ask them for what I call inside information. And what I mean by that is things like, "Who on the buying committee has the most influence? What are this person's goals? Who do you think is a blocker for this type of thing?"
So in those three things– asking for introductions, metrics, inside information–we're just asking them if they're going to put a little skin in the game and stick their neck out a little bit for us. And then developing them, I like to talk them up to their peers and to leadership, either whenever we're on a call, or when I'm recapping a call. I talk about what a great job they did and point something specific out.
The second thing I like to do is help them expand their network. Leaders are always looking to network with other leaders, sometimes inside their own company, and sometimes within their industry. Ambitious leaders are wondering where they're going to move next or who is my peer that I would really like to collaborate with. So those introductions are valuable. And then to help them by increasing their visibility, like having them on a webinar or asking them to do a podcast with us, asking them to be a panelist on our customer panel, all of that increases their own visibility. They can post that on social–it's important to them, and it's going to help them out.
And then the last thing is equipping them with resources. So either things like thought leadership that helps them with a current problem they have or to aid their decision. But the bottom line on developing them is we want to make them look good. And we also want to feed their motivation to continue to work with us.
Speaking the Language of the C-Suite
The way we sell has to reflect the way executives think, and right now, their priorities have shifted. Instead of just hearing about ROI, the C-suite wants to know how you can help them do more with the same resources. This means your conversations should focus on efficiency and productivity. How does your solution make their current team better, faster, or more effective? When you can show a leader that you can save each of their reps two hours per day, you’re not just selling a tool; you’re giving them back valuable time they can reinvest into hitting their targets without increasing headcount.
This focus on efficiency extends to customer retention. Leaders are now measured on Net Recurring Revenue (NRR), which prioritizes growth within the existing customer base over chasing new logos at all costs. The cheapest customer to acquire is the one you already have. Your account plan needs to show you understand this. Use engagement signals to identify which accounts are ripe for expansion and which are at risk of churning. When you can bring that kind of insight to an executive, you’re no longer just a vendor—you’re a strategic partner in their long-term growth.
Creating an Account Plan That Stands Out
A great account plan is about more than just a list of names; it’s a strategy for building relationships. Before your first meeting, identify three key people with VP titles in the departments you typically sell to. Your first move isn’t an email, but a thoughtful comment on something they’ve posted on LinkedIn. This isn’t about pitching; it’s about starting a genuine conversation and showing you’re paying attention. This simple, human-first approach builds rapport and makes your eventual outreach feel warm and familiar, not cold and transactional.
After you have a meeting with someone on the team, your work isn’t done. Keep the other stakeholders you identified in the loop with a short, three-bullet recap of the conversation. This keeps your deal top-of-mind and demonstrates your value as a communicator. You can build this entire multi-step strategy into your sales process using AI-powered workflows. By setting up sequences that include tasks for social engagement and automated follow-ups, you ensure no detail is missed and every key player is kept informed, all without ever leaving your inbox.
The Lesson from Krysten Conner's Biggest Career Mistake
The biggest mistake I ever made was ignoring clear red flags during an interview process and when reading about a company. And then choosing to work there anyway because it was a big-name company and one I had wanted to work with.
And I want to point out that sometimes you can see those red flags and know what you're in for. And you can just decide that it's worth it to you to have that experience or to have that name on your resume. I think for me, there would have been other ways to get where I was going that would have been a lot less painful. ]
Training and Resources from Krysten Conner
Krysten's expertise isn't just for her own deals. She is passionate about helping other sellers win by translating her real-world experience into practical training and resources. Her approach is all about "plug & play" tips you can use on your very next call. It’s one thing to hear great ideas in an interview; it’s another to have a clear path to implementing them yourself. Krysten provides that path, helping you move from theory to action without the fluff. She gives you the playbook to not only meet your quota but to build a more successful and sustainable sales career.
She offers a few different ways to learn, from direct coaching to structured courses. The goal is always the same: give you the skills to succeed faster. But learning new sales plays is only half the battle. You also need a way to execute them consistently without switching between a dozen tabs. That's where tools with AI-powered workflows come in, helping you apply new strategies right inside your inbox and turning what you learn into daily habits that close deals.
Plug-and-Play Sales Training
If you're looking for direct, personalized guidance, Krysten offers exactly that. Her coaching is built on the idea of "plug & play" sales tips—strategies you can implement immediately to see a change in your results. This isn't about abstract theories; it's about actionable advice tailored to the challenges you're facing right now. For anyone who feels stuck or just wants to sharpen their skills with an expert, this is a fantastic opportunity. She even offers a free 30-minute call to see if her coaching is the right fit for you, which is a great, no-pressure way to explore your options and get some initial feedback.
The "Deal Doubling Discovery" Guide
One of the best free resources Krysten offers is her guide, "Deal Doubling Discovery." This isn't a generic ebook; it’s a specific, 9-question system designed to help you uncover bigger deals, faster. Discovery is the foundation of every successful sale, and this guide gives you a repeatable framework to make those crucial first calls more effective. By asking the right questions, you can understand a prospect's true needs, identify larger opportunities, and create the urgency Krysten talked about earlier. It’s a perfect example of her practical approach—a tool you can download and use on your next call to see better outcomes.
Partnering with Aspireship to Launch Tech Careers
Beyond her personal coaching, Krysten has also teamed up with Aspireship to help launch the next generation of tech sales talent. This partnership focuses on creating structured training programs for people who want to build a career in SaaS sales. If you're looking to break into the industry or transition into a new role, these courses provide a clear roadmap. They are designed to give you the foundational skills and confidence needed to land a job and succeed from day one. It’s a powerful combination of Krysten’s real-world expertise and Aspireship’s proven training platform.
SaaS Sales Foundations Course
The cornerstone of the partnership is the SaaS Sales Foundations course. This program is a comprehensive, 20-hour deep dive into the skills you need to become a top performer. Taught by a team of sales experts, it prepares you for critical roles like Sales Development Representative (SDR) or Account Executive (AE). The course covers everything from prospecting and outreach to running discovery calls and closing deals. It’s designed to be an efficient and effective way to get job-ready, giving you the practical knowledge and credentials that hiring managers are looking for in the competitive SaaS landscape.
Customer Success Course
The partnership also offers a course on Customer Success skills. This is incredibly relevant, directly addressing Krysten’s point about the market shifting its focus to retention and net recurring revenue. Understanding the customer success mindset isn't just for CSMs; it makes you a better seller. It teaches you to frame your solution around long-term value and build stronger relationships from the first conversation. This course is perfect for anyone who wants to understand the full customer lifecycle and position themselves as a strategic partner, not just a vendor. It’s a smart move for any sales professional looking to future-proof their career.
Krysten Conner's Go-To Motivational Song
I mean, that has to be Formation by Beyoncé. Is there another answer to that question?
Frequently Asked Questions
What is the main takeaway from Krysten Conner's sales advice? Krysten's core message is that successful selling in any market requires a shift in focus. Instead of just pushing for new logos, reps should prioritize customer retention and expansion. She emphasizes uncovering urgency rather than creating it, building genuine relationships through multi-threading, and developing internal champions who will advocate for your deal. Her advice is about being a strategic partner, not just a vendor.
What is the "three-part demo framework" Krysten mentions? It's a simple, effective way to end a demo call by understanding the prospect's true intentions. You offer them three options to describe their situation: 1) they are just in education mode, 2) they have an urgent problem that needed to be solved months ago, or 3) they have a problem they want to solve in the next 12-18 months, but nothing is on fire. This multiple-choice approach makes it easy for them to be honest, which saves you from chasing deals that aren't real.
How does Krysten suggest finding and developing a sales champion? She recommends a "test, then develop" approach. First, you test if someone is a potential champion by asking for three things: introductions to others in their organization, specific metrics related to their goals, and inside information about the buying committee. If they are willing to help, you then develop them by making them look good. You can do this by praising them to their peers, helping them expand their professional network, and equipping them with resources that solve their problems.
What is the "three-by-three-by-three" method for multi-threading? This is Krysten's strategy for building multiple relationships within an account before your first official meeting. It involves identifying three key buying personas, engaging them with a three-step sequence (a LinkedIn comment, a connection request, then an email), and following up with a three-part plan after the meeting. The goal is to create warm connections across the buying committee so you aren't relying on a single point of contact.
How can I apply Krysten's advice if I'm struggling with deals going silent? Krysten advises a proactive approach to prevent ghosting. Every conversation should end with a clear, agreed-upon next step. More importantly, your follow-ups should always provide value, like sharing a relevant article or insight, instead of just "checking in." Using AI-powered workflows can help automate these value-driven touchpoints, ensuring you maintain consistent communication and keep your deals moving forward, even when you're busy.
Key Takeaways
- Sell to the current market reality: Executives are focused on efficiency and retention, not just growth at all costs. Frame your conversations around making their current team more productive and expanding existing customer accounts, which speaks directly to their goal of improving net recurring revenue.
- Multi-thread before your first call: Don't wait to ask for introductions during a demo. Identify three key contacts before the meeting and engage them with a simple, human-first approach on LinkedIn. This builds rapport early and gives your deal a stronger foundation.
- Test for a champion, don't just assume you have one: A true champion will invest in the process with you. Ask them for specific metrics, introductions to colleagues, and inside information about the buying committee. Their willingness to help is the clearest sign they will advocate for you.
