B2B Sales, Trust, and Why Spray & Pray Is Dead! | Katie Penner, VP Sales @ InFlu2

Episode · Sales & Trust

The Buyer's Time Matters More Than Your Quota — with Katie

You're in sales or you sell to salespeople, and your inbox proves the problem: everyone has the same intent data, the same AI tools, and the same templated "I noticed you went to that event" opener. This episode is about what still converts when everything else sounds identical.

Katie leads sales development and sells contact-level intent for a living, which means she knows exactly how powerful buying signals are — and she still gets pitched irrelevant deals every day. Her path into sales ran through early childhood education, bartending, and gifting, and every stop taught her the same lesson from a different angle: people buy from people who remember things about them.

We cover why buying software is an emotional decision (it can feel career-defining for the buyer), why the B2B world is smaller than it looks (your reputation travels through Reddit threads and private communities you'll never see), and why the single trait she hires for can't be taught in onboarding. She also walks through the metrics that leaders quote but shouldn't trust, what a no with context is worth, and the one LinkedIn message that turned a cold CRO into a permanent ally.

What you'll take away

• The trait that can't be trained. Top reps know the buyer's time matters more than their quota. When a prospect's kid is sick, the average rep pushes for a reschedule; the best rep sends chicken noodle soup and waits.
• Trust is built in public. Posting the campaign that failed, and what you learned, opened more doors for Katie's team than any win announcement. It became a real pipeline channel.
• Ghostwriters work when your voice survives the translation. A good one interviews you and converts your words into scannable text. Manufactured AI posts get detected, and detection costs you the trust you were trying to build.
• Reply rate is a vanity number. Dig into the replies: how many were negative? Check opt-out rate, manual-step completion, and call sentiment instead. A 10% reply rate with 40% "not interested" is not a win.
• A no with context can be as valuable as a yes. "No, our competitor's contract is up in four months" is a calendar entry and a future short list, if you keep the relationship warm.
• The relationship system. One hour blocked weekly for check-in messages, one personal fact remembered per person, and a calendar reminder for the things they told you they care about. The Taylor Swift concert message came from this system, and it built a connection no pitch could.
• What differentiates when everyone has the same signals. Voice notes, personalized video, and creative formats that AI can't fake yet. If your "research" can be copy-pasted from a LinkedIn profile into a prompt, so can everyone else's.

Chapters

• 0:00Welcome, Katie
• 0:32Before sales: early childhood education, bartending, and empathetic parents
• 2:44What leadership proved wrong: separating fact from feeling
• 5:12Buying committees and the emotions behind the dotted line
• 5:47Buying is emotional: trust, competitive deals, and the advisor role
• 7:43B2B is smaller than you think: short lists, Reddit, private communities
• 8:53Building trust through thought leadership — and posting the failures
• 10:50Ghostwriters, performative vulnerability, and detecting AI
• 13:39Spray and pray: pitched by intent vendors while selling intent
• 15:21What actually captures attention: voice notes, video, real hooks
• 16:38The one trait of the top 10%: the buyer's time over your quota
• 18:51Why templated outreach persists: personas, manual steps, and the skill gap
• 23:35Metrics that carry no weight: reply rate without sentiment
• 27:11Hearing no: what a no with context is worth
• 29:29The relationship system and the Taylor Swift message
• 32:53What will look ridiculous 50 years from now
• 34:03When everyone has the same signals, what differentiates?
• 36:04Sales in five years: soft skills as survival

Full transcript

This transcript has been lightly edited for readability.

Anusha: Hi Katie. So good to have you here. I looked at your LinkedIn and you've had such an impressive career. The milestones are fascinating — the amount of things you've done — and you are exactly the right person for me to ask a bunch of questions to. How do you feel about that?

Katie: I'm excited to dive in. I'm an open book, so let's see what comes of it.

Anusha: Awesome. So, like we were talking about — your LinkedIn. You've held several titles, you've dealt with different kinds of people. I want to understand: how has your life before doing any of those things shaped the way you look at people?

Katie: That's a good question. Before I started my career, I went to school for early childhood education. There's a lot of psychology baked into that, which helped inform my sense of how others may be feeling and how to address situations in the best way possible. I also think there are transferable skills in getting an education degree that led me into sales development leadership — being able to educate in a more effective way. Then, in the middle of that process, I was a bartender, and that experience helped a lot. I understood quickly what got me more tips: remembering someone's order, remembering a small detail of their life they told you about and bringing it up later. That's really where my people skills were unlocked. And even before that, I had parents who were very empathetic to others and were constantly serving the community. That shaped me into the person I am today. When we think about sales and even marketing, it's all about deeply understanding the person, what matters to them, and figuring out a way to make their life easier. The combination of all those things led me to this career choice — doing something I'm really passionate about.

Anusha: That's an awesome background, honestly — a lot of people don't have that. I came into marketing from a very technical background and had to hone my skills in understanding people; natural curiosity aside, technical was what my background was in. So it's really a skill to have something that's just in you. Is there anything you believed about building relationships throughout your childhood that, when you stepped into sales and became a leader, you were proven wrong about?

Katie: Gosh. When I started stepping into leadership roles, I was very emotional. I treated people with empathy, I was sensitive to what they were going through, and that always served me well on that end. But I had to learn to separate business — the executive conversations — from feelings. Of course you can have some emotion; you need it when it comes to something you deeply believe in. But the separation of fact and feeling at certain points is something I learned throughout my career, along with being able to take criticism without too much emotion involved. As a child, when I got criticism — maybe on a swim team — of course I took it personally, and that drove me to do better. But in business, you have to learn to separate the two slightly, and I've gotten a lot better about that. I think these soft skills, like empathetic thinking, are even more important in today's AI world, because AI is taking care of the manual tasks, and I truly believe empathy is what sets apart the humans who are succeeding today. But you have to take that with a grain of salt, know you can only be so sensitive in a business setting, and be able to take feedback without letting it chip at your shoulder too much.

Anusha: That's very true. And when I think about that through the lens of sales and business: we're all working toward a goal, and no matter what's happening in your personal life, in politics, or internally in a company, you still have to meet those goals. Which leads me to a question. In B2B, you have buyers, salespeople, marketing — a huge number of people involved in one single decision: do we sign the dotted line or not? When you look at these buying committees — B2B, B2C, whatever term — at the end of the day it's me selling something to you and you being willing to buy it or not. And there are so many emotions tied to that. It could be your own career growth. It could be your fear of looking stupid in front of your team. In your experience, how often have you seen an emotion become a hindrance to closing a deal?

Katie: I think buying is an extremely emotional experience. When your buyers are buying software, it's not an inexpensive decision, and it can feel like it will make the difference between having your job and not — the success of the software you're making your best bets on. So it's highly emotional, and it's incredibly important as a seller to earn that trust and serve as an advisor to your buyer, so they feel confident when it's time to sign on the dotted line. If at any point you lose that trust — you see this a lot in competitive deals, where a competitor claims you can't do something and you have to regain the trust — if you miss a step and don't rebuild effectively, you can lose the deal. I've seen it at a ton of different companies. People also like to buy from people they like, people they've known before, or people their friends referred them to, because there's a deeper sense of trust there. If anyone insinuates that buying is not an emotional process, they're inaccurate.

Anusha: I agree on two points. One is trust. The second: if a friend of yours had a contract with a vendor, you'd be more likely to choose them, because you have the source. But it also works backwards. If you don't like a vendor, you tell your friend, and there's no data point for that vendor to ever know why you didn't opt to work with them.

Katie: Exactly. And it's interesting, because nowadays doing your own research on a product is so easy. Buyers already have their short list by the time they're even on our radar. So it's important to have a good reputation across the whole industry, because another thing people are realizing is that this B2B tech world is a lot smaller than we think. More buyers are going to intimate community groups, to Reddit, to all these private, off-the-beaten-path places where they get answers from their peers. So that trust is really important to normalize across the company and put real effort into as you speak with different prospects.

Anusha: How do you think we can build this trust? It's a word we're all using right now, especially with AI. From your experience, what are the top ways to build trust for a company, as a sales leader?

Katie: The top way I've seen is thought leadership — really getting your team involved in sharing their thoughts, the good, bad, and ugly, publicly. This is something we started to prioritize during my time at Sendoso, and when we did, we noticed people were really excited to listen. We see posts about the wins all the time — I just got promoted, we just hit quota. It's less often you see a leader, a VP, a C-suite person say: we just ran a campaign and it failed, here's why, here's what we learned and won't do next time. That's a lot more actionable for people, and it helps them avoid the same mistakes. Once we started posting content like that, we started getting into more rooms with more leaders, because they valued what we brought to the table. It's a scary thing to do, but we realized we were driving real pipeline just by being publicly accessible and lending our thoughts to other leaders in the space. It built trust and relationships that came into the pipeline later, and it became a huge channel — something Sendoso still prioritizes today. Influ2 is doing it too. Whether it's podcasts like this or straight LinkedIn posts, these very human methods of communication — publicly telling your truth — are really powerful.

Anusha: With thought leadership being one of the things that builds trust, I can see it backfiring in two ways, which I've seen some leaders do. One: using ghostwriters. Two: performatively admitting losses — "I recently had this opportunity and turned it down, but here's what I learned about life." It becomes performative even when it's framed as honesty, because people don't see what's in it for them at the end of the day. What are your thoughts on that?

Katie: Such a good point. Ghostwriters are interesting, because I know a few really great ones who essentially meet with an exec, get the exact story in the exec's words, and are simply hired to translate that story into something readable and scannable for LinkedIn. Those ghostwriters can be extremely effective. Now, the ghostwriters who don't sound like the leader at all, or AI that's just manufactured junk — that doesn't work. People can sense the inauthenticity; you can see it and smell it from a mile away. At this point it's pretty easy to distinguish a real feeling written by a real human from detected AI or overly professional LinkedIn writing. If you're going to hire a ghostwriter, ensure your voice is still infused in the story and that you're actually communicating with them, so they can use your voice and translate it to text. But AI doesn't really have a place when your goal is to build trust — it should be written by a human. We're seeing more people focus on blogs and content still written by humans. Chelsea Castle is brilliant, and she wrote a post about this recently: the way to win in content now is to ensure it stays human, because so many people are going to AI to maximize content. The question becomes: how much of that content is actually good? I'd bet that if you're pushing quantity over quality, it isn't that great, and you're not getting many organic readers that way.

Anusha: That's so right. We have the ability to do things at scale because of AI, but once you have more quantity, your quality goes down. I've seen this happen. I was on the procurement side looking for tools for a platform I was building, and obviously I get targeted emails and outreach. With the amount of data and intent signals at hand, you can know my behavior — Google me and you'll know my career trajectory and probably what I'm worth. You could know a lot more with in-depth research. Yet I've been pitched deals way out of my budget, where I'm not their prospect at all. Big companies with all this data still reach out to people who aren't even in their line of sight — I'm not your customer and will never become one in the near future. What are your thoughts on that?

Katie: The spray and pray is getting a bit ridiculous, in my opinion, with the access to AI and automation tools for outbound. I sell contact-level intent, so I know how powerful the signals are — and yet every day I have other intent players trying to pitch me. So I totally empathize. It goes hand in hand with what we said about content: it should be all about quality over quantity right now. As a buyer, I get hundreds of emails pitching me a day, tons of LinkedIn messages, phone calls, and I've learned to ignore most of it. The only way to capture my attention these days is a personalized voice note on LinkedIn, a personalized video, or an email that starts with a hook showing you've done your research. I've talked to my peers who are in purchasing decisions, and that's how people are capturing attention. Even out-of-the-box things like direct mail campaigns that are fun and unique — that's what ultimately gets you the win these days. Now, AI has its place. We have a tool internally that aggregates first-party signals and signals from Influ2 — of course we drink our own champagne — and we use AI to take all the activities someone has done and summarize what must be most important to them. Then we take that and write the email ourselves. It can be really helpful. But the mass blasting has gotten to a point where only the really human activities help you stand out today.

Anusha: That's true. Take your top 10 salespeople. What's the one trait — something no training could ever teach, something they have inherently, the way you have psychology in your background from childhood — that you've seen in the top 10% you've hired?

Katie: I think it's knowing that the buyer's time matters more than your quota. That's a very hard thing for a lot of reps to understand. One of the mistakes I see over and over with SDRs and BDRs is that they push too hard for time when it's inappropriate, and they push the buyer away forever. Versus: "Hey, no worries. I know something's going on with your kid, they're not feeling well. We'll cancel this meeting, and I'll follow up in a few days, whenever they're feeling better." And instead of hounding them for time, thinking more creatively: their kid is sick, why don't I go out of my way to send some chicken noodle soup to their house as a meeting reminder, and say, "Would love to reconnect whenever your kid is feeling better." Taking that extra step to maintain the relationship, versus only thinking about you and your quota. Ultimately it goes back to soft skills. Everything that's hard to teach falls back to a soft skill — empathy, listening. As a leader I can do my best to explain what went wrong in certain situations and how we should have done better. But whenever I'm hiring now, those are the skills I'm looking for, because they're very hard to find in a person and very hard to teach. It's better to find someone who has those qualities up front and then teach them the operations later.

Anusha: I find that so interesting, because I've seen a lot of SDRs and BDRs send me emails so out of touch with reality — I can tell it's templated — and these are companies that are really good at sales, leaders who are really good at thought leadership posts. Yet the emails I get show no research on who I am. A simple Google search tells you who this person is; if you can't find them, they're probably not the decision maker for whatever you're selling. Why do you think that happens? Is the personalized, get-to-know-their-family treatment only for the top 10 accounts? What's the gap?

Katie: Most orgs have generic sequencing. They have a quota — they want 100, 200, 300 people going through sequences every day — so it boils down to a workload issue. Now, what I don't understand about situations like that is why the leadership team wouldn't create multiple sequences by persona, so it at least feels relevant to you. It may not be personalized, but it will be relevant — a called-out pain point that people like you are facing, or case studies relevant to people like you. If you're going to sequence at scale, it should at least feel relevant. And I understand sequencing at scale is necessary — you can have quality and a certain level of quantity — but to maintain both, you need different messaging tracks for different personas at the very least. I also think: bake manual steps into those sequences to allow for a bit of personalization, hold your SDRs accountable for doing it, and give them the AI tools to do it quickly so they're not spending 30 minutes on each email. We have everything we need for AI to pull those personalized, relevant facts. So why are we still seeing this today? I think it's simply a lack of understanding of how AI can help optimize outbound in a way that's still scalable.

Anusha: It's even more interesting to me because I use AI a lot for my own outreach — I run this podcast and reach out to people every day. I believe in using AI to give me a list of people who qualify. But then I go through each of their LinkedIn profiles to see what they're talking about and what they're interested in, so when I reach out, they feel like I know them — not that I'm reaching out because they have a certain title at a certain company. What I don't understand is: as one person running a whole podcast, I can do that. Why can't a big company, with people hired specifically for this, do it? What's the bottleneck?

Katie: The good reps do it. That's the bottom line. You can make all the excuses in the world — high quotas, tens of thousands of people in their book of business — but you'd find the best reps are doing it, their quality is higher, and therefore they're converting more. Some reps get overwhelmed by the volume in their book and start sending generic emails. It's a lack of understanding that more emails doesn't necessarily mean more conversions. People need to understand that the human touch is what's converting today. Unfortunately, I think it's a skill gap more than anything else.

Anusha: I also think when salespeople are given quotas, they start focusing on metrics — I've sent this many emails, this many opened, this many in pipeline. When they talk like that, what about those metrics tells you the relationship is not actually progressing the way they think it is? Just because someone opened an email doesn't mean the relationship moved. What's the one metric people often talk about that carries no meaning or weight at all?

Katie: A lot of people will talk about reply rate, but they don't dive into what those replies were — and a lot of them can be negative. I also don't see a lot of people talking about opt-out rate. If you have a sequence with a high opt-out rate, you're probably damaging the relationship rather than helping it, and that's something to check on all the time. Something we're also looking at internally, and that more teams should look at: how many manual steps were actually completed and executed by the reps, and what was the quality of those manual steps. You can't see that in a dashboard — it requires deeper digging. It's harder, but you need to actually look at those manual emails, understand how your reps are filling in the relevant personalized information, and coach to that. Call sentiment is important in the same vein: what were the objection reasons, what are we currently dealing with, so that as a leadership team we can come up with replies to those objections that will land well with prospects.

Anusha: How often do you think people do that? And why haven't they implemented it already — what's been the friction all along?

Katie: Your basic platforms show you the overarching stats — reply rate, opt-in, opt-out rate, open rate, the very basics. Leaders have taken that at face value: "Our reply rate is 10%, that's awesome, keep the sequence going." Versus actually digging into those replies and saying: wait, four of these ten were "not interested" — that's not a positive reply, so let's not count it as one. It's just not digging deeper. And this is where AI can be really useful — it can do these deep dives for you. Okay, of that 10%, really 60% were positive or wanted more information. How can we adjust our messaging to avoid the 40% it didn't resonate with? What were those personas, and is there another sequence we could create specifically for them that would land better? It probably ends up being a bandwidth issue: before AI, digging into all the stats of all the sequences required a lot of manual work, and SDR leaders are managing 10 or 20 people, if not more. Time is rare. But now, with AI, we have the tools. Hopefully more leaders start to really understand the sentiment behind these stats and dive deeper.

Anusha: When you see reply rates, or you take phone calls and people give you a negative response — no is one of the hardest things to hear. I hate hearing no. As someone who reaches out to people every day, when people say no to being on the podcast, it takes a hit. But this is your career — you live it. In your experience, you've seen the patterns: people say no not for the reason I imagine, but usually for some underlying reason. Is there anything common that stood out to you?

Katie: I think getting a no with context can be almost as valuable as getting a yes. If you get a no and you ask the right questions to understand it — for example, it's a no because they have a competitor whose contract is up in four months — great. Now I know exactly when to reach out. If I play it correctly and we build a relationship, I'll probably be on the short list when they re-evaluate that competitor. Or if it's a no because they're too early-stage for a tool like mine, maybe I can give them advice based on other companies I've seen grow from where they are to where my customers are today, and build the relationship that way. Sales is a long-game relationship play. Turning nos into opportunities for relationship building can be really powerful, and that's what the best reps are doing today. They're not just waiting for hand-raisers and booking meetings with those people. They're building year-long relationships that come back to them when a buyer builds a short list, or joins a different company and suddenly needs your solution. You're top of mind. That's what drives the most successful salespeople today.

Anusha: And I barely think those relationships are formed because you sent the perfect pitch or a volume of emails. It's mostly one moment — you met them at an event, or you gave the right response. In your trajectory, what's the one thing that stood out — the reason you've been able to hold on to relationships across companies?

Katie: Gosh. It's a combination of staying visible to the network I've built — sharing on LinkedIn, commenting on their posts, keeping the rapport that way — but also making a point of it. I have an hour-long block every week to send LinkedIn messages to old friends I haven't talked to in a while, checking in on people. I also make it a point to remember at least one thing about each person I meet at a work conference or share a stage with. I try to find out something about their personal life. Psychologically, we know people like people who let them talk about themselves. So I always ask about their family, their hobbies outside work, what their 5-to-9 looks like, and I get a ton of great information. That comes from my background in gifting — we'd go to events and talk to people to get gift ideas to send afterward. But it's still so valuable even when gifting isn't the objective, because I can check in. There was a CRO, for example, and I learned that he and his wife were going to a Taylor Swift concert, back during the Eras Tour. I learned about it months before they went, kept it in mind, and put it on my calendar so I knew exactly when they were going. Months later — we hadn't talked in months — I pinged him the day after: "Hey, how was that Taylor Swift concert? I can't wait to hear all about it." He was so impressed with the timeliness of the message, that I had remembered, that now we have this inside joke forever. Those things are incredibly powerful, because I know if I messaged that guy needing someone to contribute to an article or come talk to my team about the life of a CRO, he'd do it in a heartbeat. We built a human connection, and he knows I cared enough about him to care about the things he cares about — beyond him as a CRO with the ability to buy my products. As humans, we want to be cared about beyond our ability to pay for software. If you can show that to somebody, be believable, and mean it, that will take you very far. At the end of the day, it's about being thoughtful, putting in the effort, and considering this another relationship — not something transactional. And that gets really, really lost in the business world.

Anusha: Absolutely. When you think about sales 50 years from now — someone's writing a book, looking at everything we've done in sales and marketing — what do you think they'll point to and say, "I can't believe this is how they did it"?

Katie: I think the generic spray and pray is going to be a thing of the past. There is no reason — with AI capabilities in a couple of years, with everything that's publicly accessible data, with all the signal tools out there — that anything hitting a prospect's inbox should be generic. We're going to think that was ridiculous. And I think sales in a few years is going to be even more exaggeratedly about relationships — probably more in-person meetings to continue relationships, more events, more face-to-face human time. That's what we're going to prioritize in the years to come.

Anusha: But I also think about this: since we all have access to the same intent and behavioral signals, every message is going to start sounding the same. "Hey, I noticed you went to this event last month, hope you had fun, let's talk." Without AI, that would have sounded like I did my research. Right now, I could copy-paste someone's entire LinkedIn, give it to Claude, and say "find something that stands out about her" — and I might not have even noticed those things myself. So how do we differentiate between "this person actually put in the time to know me" and "this person is doing their cold outreach"?

Katie: The reality is buyers are going to self-serve more than ever, so our chance to sway their opinion and get on the short list is going to become smaller and smaller. This goes back to what I said about how people capture my attention, and my leadership friends' attention: the things AI cannot do, at least right now. Video messages, voice notes. I've had people send me whiteboard flows of how they could help me and what they could build. It's all going to come down to creativity. Fewer people are going to answer the phone, fewer people are going to answer emails. But if you can get face time via video, or even a voice note, and differentiate yourself that way, you'll see more success. We're seeing that trend on my team right now — people are loving the videos where they can actually see the person's face.

Anusha: Is there anything you want to talk about that I didn't ask you?

Katie: My gosh — if you could tell me what sales is going to look like in five years, that'd be great. No, ultimately the only thing I know is that remaining human, authentic, less transactional, building relationships — that will remain true. It will remain one of the strongest skills salespeople can have, now and five years from now.

Anusha: Very true. We talk a lot about this, but in action it's like maintaining a friendship or a romantic relationship — it requires the same kind of effort. We have to keep that in mind and not think "it's just about this company and this one account." It's about maintaining the relationship wherever you go.

Katie: Right. And — I'm just starting to think deeper on this — today and in years past, people who didn't necessarily have soft skills were able to survive in sales because there was a repeatable email process. They could throw people into sequences, let them auto-run, and get some meetings, because that's how email worked. People weren't getting slammed by automation tools then. But now, and five years from now, I think we'll see those soft skills becoming important for survival in this role. It's going to become more important than ever, and again, it's not easily teachable — it comes naturally, learned throughout your life growing up, being raised, all of that. It'll be interesting to see how everything shakes out. But if I were a betting woman, that's where I'd place my bet.

Anusha: It's interesting, because now more sales leaders are going to say that, and people will think: okay, I need to ask better questions — which means I'm going to ask ChatGPT what questions to ask. That's going to be the next trap. People will fool themselves into thinking they know what questions to ask, and a few years later they'll realize it's really difficult, because you don't always get the answers you want. Then you have to pivot and think quickly on your feet, and that's not something you can learn. Like you said, it has to be an inherent quality. You have to be the annoying nerd kid in the classroom going, "Hey, I don't understand what you meant by that." You really have to be that kid.

Katie: Yeah, I think so too.

Anusha: This was great. Honestly, I have never had a sales leader on the podcast before. This was awesome for me, because I've had these questions in my mind for the longest time. Thank you so much for doing this.

Katie: Of course. Thank you for having me. This was so fun.

One question before you go: what's the most memorable cold outreach you've ever received — the one that made you actually reply? Comment and tell me. I read every one.