In this episode of Beyond SaaS, Jason Niedle speaks with Sam Basile, Vice President of Sales at Skillfully, about innovative solutions to hiring challenges and the importance of mental health in sales leadership. They discuss how Skillfully uses AI to create realistic workplace simulations for hiring, the company’s mission-driven approach, and the significance of partnerships in growth strategies. Sam shares insights on navigating the AI landscape in hiring and the evolving buyer-led market, emphasizing the need for companies to adapt their sales strategies accordingly.
Takeaways
- Focus on mental health as a sales leader.
- Skillfully transforms hiring with realistic simulations.
- Partnerships are key to growth opportunities.
- AI tools should be evaluated for depth and effectiveness.
- Sales strategies must adapt to a buyer-led market.
- Understanding customer buying behavior is crucial.
- The importance of showcasing unique applicant skills.
- Navigating the AI landscape requires education and clarity.
- Salespeople should leverage third-party endorsements.
- Growth strategies should align with community benefits.
Sound Bites
“fixing your hiring challenges”
“focusing on my mental health”
“the race to add powered by AI”
BeyondSaaS Transcript
Jason Niedle (00:00)
Today we’re talking with Sam Basile, Vice President Sales of Skillfully about fixing your hiring challenges so you can supercharge your growth.
Welcome to Beyond SaaS. I’m Jason Niedle, founder of Tethos, and we solve growth problems for tech companies, kind of like a fractional CMO that comes with a team.
Today I’m excited to chat about growth with Sam. Sam is the vice president of sales at Skillfully. And Skillfully does this amazing thing where they allow companies to hire for real skills, not just for resumes. And I wish I had this many years ago. They provide realistic workplace simulations supercharged with AI that actually transform the hiring process. So much so that they’re actually a public benefit corporation.
And Sam is a highly experienced sales leader. He began in door-to-door hospitality sales. And I saw that you went to the culinary school, so you’re probably a great cook on top of all the business acumen you have. Before you moved into tech, colleagues note your knack of turning tough cold calls into long-term partnerships by listening. So I really can appreciate that methodology. Welcome, Sam.
Sam Basile (01:03)
Thank you so much, Jason. Great to be here.
Jason Niedle (01:06)
Yeah, I’m
excited. And thanks for calling in from Maine. I kind of wish I were there today.
Sam Basile (01:10)
Portland, Maine. It’s the place to be in mid-July. I will say in April and May. It’s not as fun as mid-summer.
Jason Niedle (01:18)
Hey, before I forget, have you got a golden nugget, a quick tip for us?
Sam Basile (01:21)
You know, I do. I think in today’s day and age, everyone is stressed to the max with what they should do. Wake up at five, do this, cold plunge. There’s so many different things that we’re all doing. And one thing that I’m doing is really focusing on my mental health in 2025 as a sales leader, especially, in a startup, it’s extremely, extremely stressful and making sure that I’m healthy
and kind of consistent is the key. So I have actually just partnered with Dreamfuel, which is founded by a neuroscientist that’s really focused on kind of implementation of mindset tactics within business for executives. So in very high stress, high strong situations, you can kind of move through it. that’s my
golden nugget not necessarily a tool that I’m using to help me day to day but something to do much more than just professional help. It’s kind of helping me all around
Jason Niedle (02:15)
And Dreamfuel, what exactly is Dreamfuel?
Sam Basile (02:18)
So Dreamfuel, like I said, founded it from neuroscientists. So they have a collection of tactics. It’s these practices that you can do kind 10 minutes a day that allow you to really hone in on your focus, really stay in that state of flow so you can get more work done and really not rely as much on any kind of whether it’s caffeine or anything else, you can really kind of produce all that internally. So that’s the goal.
Jason Niedle (02:33)
Mmm.
I love that. That was a huge tip for me earlier this year. And you just brought back a memory that I need to be more cognizant of getting into flow. And I had someone say to me, write down the things today, just write down everything, those moments when you’re in flow and then there’s moments when you’re not. And then add to this list of for a few days. So I did it for about a week and then they were like, why are you not in the flow more? Start saying no to all those things on the left list and yes on the things on the flow list. And when I even just increased that by 20%, I mean, everything was completely different.
Sam Basile (03:07)
love that.
Jason Niedle (03:12)
It was magical and I was happier.
Sam Basile (03:14)
I love to hear it. know, it’s one of those things where it’s like when you’re working at a larger company, it’s easier to get into flow. Systems are in place, everything is kind of there, right? And when you’re building, it’s really difficult to come up with that flow. So leaning further into that by kind of working with the DreamFuel guys has really started to help me for sure.
Jason Niedle (03:31)
I’m going to look
that
Jason Niedle (03:32)
Hey, it’s Jason with a 10 second note from our sponsor, Tethos. I wanted to offer you our Hypergrowth Playbook. It’s a free guide that I put together, a compilation of our first 20 or so episodes of learning from the show, which includes book recommendations, golden nuggets, and the amazing learnings from all these tech leaders. Simple to get it, just drop the word GROWTH in the comments and I’ll send it to you, or head on over to tethos.com/playbook and that’s T-E-T-H-O-S dot com slash playbook, and you’ll have it right there. All right, back to our episode.
Jason Niedle (04:02)
Skillfully sounds amazing. Tell me how this works.
Sam Basile (04:04)
Yeah, so picture pre-hire assessments, right? If you think about historically what an assessment tool really is, it’s either you think of maybe a personality test or you think of maybe like multiple choice questions, right? You’re just trying to get an understanding of who this applicant is beyond the resume. And while that may have worked for a period of time, assessments have really come a long way. And so what Skillfully is doing is really leading the market in terms of what’s available pre-hire. So what we’ve done is
Instead of, like in an interview where you ask someone, tell me a time when you overcame a challenge or tell me how you build relationships in a sales call just for a sales role, right? Instead of asking those questions in a resume, what Skillfully does is put people in a job-specific simulation that mirrors the day-to-day work that they’ll do in the job they just applied for. So now for an employer, they don’t have to rely on
AI generated resumes and this overwhelming applicant volume that everyone’s dealing with right now, what they’re able to then do is have right at the top of the funnel applicants go into that skill assessment and we can organize all of their applicants based on that demonstrated proficiency. So now they can say, wow, we had a thousand people apply, here are the top 200, let’s reach out to them first. Now we know where the best applicants are. So really doing a lot to try to
Jason Niedle (05:18)
Mm.
Sam Basile (05:24)
bring recruiters back to building relationships with potential applicants rather than having hundreds of 15 minute phone calls to see if someone’s resume sounds, you know, if they sound like what their resume says, they should sound like it’s, the process is broken and our goal is really to provide some clarity there.
Jason Niedle (05:44)
Yeah, you just gave me a realization again. It’s like, let my AI talk to your AI so we can decide if you should come in so that a real human can decide that you weren’t the right person in the first place. It’s the traditional way, right?
Sam Basile (05:55)
Exactly, exactly. And usually that happens like in the interview. So now you’ve got hiring managers that are taking time out of their day and within five minutes they’re like, how did this person get on my calendar? You know what I mean?
Jason Niedle (06:05)
Or
they’re so good at being able to get their way through, they get in and then you discover a month into their training that they weren’t the person that you thought they were and you’re screwed because now you’re two months behind where you needed to be.
Sam Basile (06:15)
Exactly. And you Jason, that you nailed it on the employer side. I think the cool part is for the applicant side, what’s great about it is now instead of only having to rely on a resume and a cover letter to really pitch who you are, you can actually showcase some of the things that are unique to you. Right? Like for me, when I speak, I use body language, I use my hands a lot. You know, my, my tone goes up and down. Those are things that you can’t get from my resume. Exactly. Exactly.
Jason Niedle (06:40)
You mean that doesn’t come across in your resume?
So it sounds like you’re a mission driven company, you know, with the public benefit. Tell me a little bit about that.
Sam Basile (06:48)
Yeah, so our founder, Brett, actually started Portfolios with Purpose as a nonprofit organization to essentially help,
under-service communities within college showcase and kind of hone in on their skills. And so it was really more of a learning environment where Brett was, you know, he was historically in finance. And so when he came out of finance, he started to really give back to the community and build people up to go into the world of finance. He really focused in on creating these simulations for the seniors in college to sharpen the blade of kind of their terminology,
and how they should go into an interview with a finance company. And after a little while of doing that, some of these larger employers, Barclays, TD Bank said, hey, what you’re doing here, are you able to do actually for our hiring practice? since then, Skillfully was born, right? And since then, we’ve kind of added in the addition of AI in all these other areas.
Jason Niedle (07:38)
nice.
I love product market fit when it comes from demand, because the demand literally made the product.
Sam Basile (07:50)
Exactly, exactly. And so now we really want to make sure that,
while we are doing as much as we can to help the employers, that public benefit is there for us to really make sure that we’re giving back and really highlighting those applicants that potentially those keyword, within your ATS, right? All those keyword searches within the resume, if it’s not perfect, you’re going to get removed from their ATS. You won’t move forward in the interview process. And what we really can help do is also highlight some hidden talent pools that are already applying.
Jason Niedle (08:19)
Totally. So how are you growing? What’s your KPIs? What are you looking at? If public benefits are slightly different in some ways, how does that affect your metrics of what you’re looking at and how you’re growing?
Sam Basile (08:32)
we really look at the full picture, right? So if I’m focusing right now on helping high volume staffing companies who are feeling the pain the most, right? They’re having to place so many people over the course of one year that they really feel the pain of what we can solve. And so if I’m focusing on that area, I have colleagues that are on the university and workforce development side that are partnering with companies like Anthropic and local colleges to
essentially showcase existing talent that our seniors in college that already have the skills to go into employer like Anthropic or like a Salesforce or really any other employer, right? So it’s looking at both sides. It’s, great, we’re going to be helping our customers on the employer side, but we’re also going to make sure that a large portion of our focus is really giving back to the community and kind of helping create a more balanced
ecosystem within hiring. Think everybody knows hiring is broken and so we’re hoping to be a first step.
Jason Niedle (09:30)
So I hear in there that you have or could have two ICPs, right? You could have large companies that hire and you can have staffing companies. How do you look at that?
Sam Basile (09:38)
You know, I look at our ICP in three separate ways. Some of our secret sauce that I’ve started to identify in 2025 in particular. We essentially have three. One is really that staffing category. Two are direct employers, Kind of any software company that has sales, customer success, support, accounting teams, marketing teams, really any of those roles could be great fits for our simulations.
so then the third one would really be partnerships. I think that partnerships are really one of the biggest opportunities for us this year. I think in 2025, what you see, Jason, is buyers want a trust layer, right? Whether that trust layer is they do a free trial on their own or they already have someone that they trust that suggests the
tool that refers skillfully, right? So I think resellers finding, for example, fractional CHROs that are, going from company to company to company, they’re coming in as the trust layer. I partner with that fractional CHRO and anytime they go into a new org that says, wow, we’re really struggling with screening and kind of our applicant volume, that’s when that CHRO can say, great, I already have a partner that I trust to fix this challenge.
And so that’s really what I see as kind of like our ICPs, but also even a strategic advantage for 2025.
Jason Niedle (10:56)
And you mentioned secret sauce, so I gotta know what is that
Sam Basile (10:59)
That secret sauce is really just what I mentioned, right, those partnerships.
Pre-2023, I think people thought of partnerships as maybe 20% of their business. I truly believe that partnerships moving forward are going to be a much larger percentage of revenue because of that trust layer. So if right now I’m trying to build trust through marketing, podcasts, third party reviews, that’s one way you can build trust. But another way is to already have
Jason Niedle (11:08)
you
Sam Basile (11:27)
you know, someone internally at that company that already trusts your product, right? So the partners are in for us.
Jason Niedle (11:32)
Yeah, 100%.
So if we look at the constraints, what’s holding you back from your growth goals or what could you change that would supercharge your growth goals?
Sam Basile (11:41)
You know, it’s interesting, Jason, when I was looking at this question, I was really thinking of like, should I answer this about something internally or should I answer this externally? And I kind of want to make it external because I think a lot of your listeners are in a similar situation where in 2023, there was a race to add powered by AI to your website, right? And exactly, I think we’re still, we are definitely still in the race. And so then the question becomes,
Jason Niedle (12:03)
Still today. Yeah.
Sam Basile (12:10)
In 2025, now that every tool has AI in it and every vendor is seemingly able to spin up new products that much faster, which tools and which vendors are just kind of chat wrappers versus ones that have proprietary pieces on the backend. And I think when you start to look at the macro environment of what my biggest challenges are, it’s that
we’ve been working on Skillfully now for about four years and almost five years now. And so when I talk to a customer or a prospect, I should say, they’ll say, yeah, you know, we heard from so and so and so and so who’s doing something similar. And I think the key word is similar, right? And so what that requires me to do is spend more time educating on how we aren’t a surface level, you chat wrapper. We’ve really done the hard work
to produce something that is scalable and has kind of the longevity that I think a lot of these other AI nice to have tools won’t end up.
Jason Niedle (13:13)
That’s interesting.
I guess that can happen through messaging, through educating through podcasts. What other ways are you kind of breaking that down? And I guess ultimately, in a way I could argue, it doesn’t matter if it’s a wrapper or it’s proprietary, right? Because I want your argument to be, yeah, no, but we’re this much better. Like how are you that much better because of that?
Sam Basile (13:33)
I think when you think about a wrapper, right, the wrapper could be, I don’t want to dog a different industry, but like, if you think about a nice to have, like a note taker, right, a tool that joins the calls, takes the notes, and transcribes them for you, right, those have popped up.
They’re all over the place. There’s a million of them, right? And so if you think of that as a surface level tool, then you have other providers, the larger ones in that case, that are doing maybe two or three levels deeper than just that one instance, right? So take us, right? There are other tools where you can have interactions or you can have kind of role plays. The challenge with those is they may hallucinate, right? So what we’ve done on our side is,
You know like when you say, when you ask a prompt to a chat GPT and it gives you a response, that’s really one LLM.
And so what we’ve actually been able to do is stack LLMs on top of one another so that we can have long-form conversations with very minimal hallucinations. And so for me to get that technical about AI, which is already a topic that people are really struggling to get up to speed on, It’s challenging to differentiate what’s that surface level note-taking tool versus the one
like ours that’s four years in development with 30 different LLMs that are behind it constantly reevaluating the conversation. It’s that level of technical knowledge that needs to be discussed to showcase the difference and I think that that’s the hardest part right now is nobody really wants to hear that from me. I’m the sales guy, no one wants to hear that from me. And so what we’ve been finding is we worked with a company called Hacking HR that
Jason Niedle (14:51)
Wow.
Sam Basile (15:11)
they had a unique offering where they have, essentially one of our customers host a webinar of how they solved their screening challenges with us. And so it’s hosted by Hacking HRs, not affiliated to us. And the presenter is a customer of ours, but again, really not affiliated. They’re just saying, here’s the problem we had and here was the tool and the vendor that we chose to fix the solution and here are the outcomes.
Right, so now we’re able to tell the story without me, the salesperson, really saying anything. And that’s the most important piece is we want people to understand that what we’re offering really will benefit you. And when the salesperson says that, it comes across as just me trying to sell you, as opposed to my genuine reason for reaching out is because I know you’re struggling with something that we can help you,
so anyway, finding a third party to actually be the one to deliver that message has really changed the way we’re able to communicate and educate that larger audience.
Jason Niedle (16:12)
I think this here could have been a golden nugget as well because it’s such a great way to look at things. My wife’s a singing instructor, right? And so for a long time I’ve been talking about her, set up your own podcast, set up your own podcast. And then the other day in something very similar to what you’re talking about, one of her students was asking her all these questions. And I was like, you know what? What if your students ran and owned their podcast and they ask you and other teachers and other experts,
producers and you know, we can get all these people on the phone with them, but you’re kind of like the primary character, but they’re the ones doing the asking and A, they’re going to ask the right questions, right? B, they’re going to be trusted by all their peers because it’s not coming from you. So like any business and almost any niche can use what you just said of how can we take a third party and have it show us how it’s working for them and what’s going on and ask you the questions that they want to know instead of running it on our side. I love that.
Sam Basile (17:03)
Exactly. It’s like, sure, we had Hacking HR that had this set up that we found, but you could find anyone to host a webinar, right? And you could grab your own customers to be the one, to be the presenter, right? So I think it’s definitely a strategy that can be replicated in any industry for sure.
Jason Niedle (17:18)
Yeah, really
smart. That’s awesome. So what do you wish other leaders knew about growing sales?
Sam Basile (17:23)
what’s really challenging right now in sales is that it’s buyer-led. You know what I mean? And the buyer’s preferences are changing as quickly as the technology is changing. And so, you know, Jason, you know the deal, right? Phone was king, right? Then email’s king, okay? Then, you know, we’ve constantly just always had something that’s worked really well.
And I think right now we’re experiencing a few things that were okay, as opposed to one channel that’s really, really doing really well. And so that’s, think, what’s difficult in sales, right? What’s difficult in sales is, especially in 2025, everything has changed. And so what can we do to kind of get around this? Personally, to me, I think it’s the free trial motion. Like I said.
It’s a buyer-led world, and the more that you can enable potential buyers to go in and understand what your product does on their own time without having to talk to me, the salesperson.
there’s all these stats that 90% of the decision is made before they even talk to me. It’s really then all about enabling the 90% of the decision that’s made without the salesperson. How can your website do those things? How can you increase the conversions from website viewers to maybe a free trial, then to a paid subscription, then to an enterprise agreement? And so it’s understanding
how you’re…
customers are buying and then aligning your strategy to how they’re buying this year. My last note on that is, you my CTO the other day said that he was like, I feel like any tool that we’re using in GoToMarket that was built, pre 2020, we shouldn’t even use because it doesn’t make sense for how people are buying today. And I don’t mean that as a dig to all of these, you know, legacy products that I know and love.
But it’s kind of true, right? I think some of these smaller vendors are moving really, really quickly and creating things that are working right now. And it’s a matter of will those channels end up being as successful as cold calling or as emails were historically? Time will tell, but I think PLG motion is really the way that buyers in 2025 want to buy.
Jason Niedle (19:40)
So I feel like part of all these AI tools are just hacks on the old tools. Like there’s email and now there’s an AI tool to hack the way that email kind of used to work. So you make it still work a little bit. And some of the phone tools are hacking phone tools. But on the other hand, we’re absolutely in a new world. And I think we need to have all these things and we need to make them somehow all work in a universe.
And that’s a little bit of the hard thing too, because there might be 25 different things that we need to be doing and yet your marketing team might be two people or whatever and we’re trying to figure out how do we conduct this orchestra when none of it at the moment is particularly well connected. And I think that’s really interesting. And we even have that problem here, right, in a marketing firm of, okay, we need to do all these different things and how do we coordinate them because there’s no overseer other than humans. Which I find just super fascinating.
And then the other question I keep thinking about as I talk to people on the show is there’s AI native organizations. There’s organizations that have amazing tools and said, stop everything. We’re going to go AI native and they have to figure out like, how do I start over in a way? And then there’s the people who come and kind of layer the AI sauce on top of whatever they’re doing. And how do we choose those methodologies and how do we get into one or the other is a really fascinating business problem for I think
Sam Basile (20:47)
Yeah.
Jason Niedle (20:50)
every tech company right now.
Sam Basile (20:51)
Agreed, I think fortunately a lot of those vendors have monthly agreements or some good trials. So you can kind of jump in, get your feet wet, see what it does for your organization, and then back out if it’s not the right play. And I think that that’s really what the next couple of years are going to be as the technology advances every six months. It’s really going to be, OK, so is what we did in January still relevant in September?
The jury’s still out, you know, we may not know. And so I’m really excited to see what the year brings, that’s for sure.
Jason Niedle (21:19)
Hey, I know you’re on a deadline. Any final thoughts before we let you go?
Sam Basile (21:23)
My final thoughts are if you see AI tools, start to identify is this surface level or has this company really gone above and beyond to
really fix a problem, right? And really create a solution that’s multifaceted, that isn’t just a point solution, right? I think there’s just so many point solutions. It’s gotta have more than one benefit. And so I’m really excited to see the noise of tools that are being created go away once people start to get annoyed by that fact, right? So I’m just really excited to see where we go with all this.
that new tech.
Jason Niedle (21:57)
Awesome. And where can our audiences find you?
Sam Basile (21:59)
So you can find us at skillful.ly or you can find me on LinkedIn, Sam Basile, B-A-S-I-L-E.
Jason Niedle (22:08)
That’s
skillful, S-K-I-L-L-F-U-L dot L-Y. Sam, thank you so much for being on Beyond SaaS. For tech leaders out there, we’re committed to exploring growth. And so we drop episodes twice a week on Tuesdays and Thursdays. And you can find me, Jason Niedle, at tethos.com, T-E-T-H-O-S.com. Until next time, this is Beyond SaaS.
