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Home/The SaaS Podcast/Episode 182
Consultative Selling SaaS Built $5M ARR With No Inbound
Oleg Rogynskyy, People.ai

Consultative Selling SaaS Built $5M ARR With No Inbound

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Episode Summary

Oleg Rogynskyy bootstrapped Semantria to $5M ARR in just two and a half years using consultative selling SaaS tactics - with zero inbound marketing. His rule: ask five questions before giving one answer.

In this episode, Oleg shares how he sold a product that didn't exist for nine months, landed million-dollar enterprise deals through extreme listening, and then applied the same consultative selling approach to build People.ai, which got almost 100 logos in its first 45 days.

Oleg Rogynskyy is the founder and CEO of People.ai.

People.ai is a SaaS platform that uses artificial intelligence to help sales teams to be more effective by automatically capturing all their sales activities and then giving them clear and actionable insights.

People.ai was founded in 2016 and has raised around $7 million in funding.

But back in 2010, Oleg was doing the 9 to 5 at another company, when he had an idea for a startup. He realized there was a need for democratized, cloud-based text analysis. So he left his job to bootstrap a startup called Semantria.

It took Oleg and his co-founder George about 9 months to build the product and to land their first customer. And Oleg spent the majority of those nine months talking to prospective customers using a consultative selling approach. He focused on two main things - listening more than he was talking and providing his prospects with real value before even talking about his product.

And that approach paid off. The founders went from zero to $5 million ARR in just over 2.5 years. And they did no inbound marketing. They just focused on doing one thing - outbound sales really well.

Topics: Founder-Led Sales|First Customers|Enterprise Sales

Key Insight

Oleg Rogynskyy bootstrapped Semantria from zero to $5M ARR in 2.5 years using pure outbound consultative selling with no inbound marketing. His method - asking five questions before giving one answer and never showing a demo before the third or fourth call - landed million-dollar enterprise contracts and later helped People.ai sign nearly 100 logos in its first 45 days.

Key Ideas

  • Oleg spent nine months selling Semantria before the product was fully built, using customer conversations to shape the roadmap in real time
  • His consultative selling rule: ask five questions before giving one answer on every sales call to stay in discovery mode
  • At People.ai, demos are not allowed until the third or fourth meeting to ensure deep understanding of customer problems first
  • The first enterprise deal at Semantria (with Sprinklr) took six to eight months of daily Skype conversations and was worth over $1 million
  • People.ai signed almost 100 logos in its first 45 days by turning customer development conversations into a working prototype in two weeks

Key Lessons

  • 🤝 Consultative selling SaaS means asking before pitching: Oleg's rule of asking five questions before giving one answer kept him in discovery mode on every call, letting him position the product using the prospect's own language and pain points.
  • 🧠 Deep preparation makes consultative selling SaaS work at scale: Oleg spent an hour preparing for each call with 5-10 page research documents covering the prospect's blog posts, Twitter history, previous companies, and mutual connections.
  • ⚡ Ship features without announcing them to build trust: Oleg quietly shipped feature requests from Sprinklr's CTO, letting them discover improvements organically. This created a feedback loop where the customer saw ideas materialize in two weeks.
  • 🎯 Use consultative selling to validate before building: Nine months of selling a product that didn't fully exist gave Oleg real market data to shape the roadmap. The customer conversations were simultaneous product development.
  • 🚀 Turn customer development into rapid sales traction: At People.ai, Oleg interviewed hundreds of VP Sales, built a prototype in two weeks based on their feedback, and signed almost 100 logos in 45 days before Y Combinator demo day.
  • 📉 Horizontal middleware SaaS limits your exit options: Semantria reached $5M ARR but operated in a $100M global market too small for VC interest, leaving Oleg with only two options - stay small or sell.
  • 🤝 Create social capital to earn referral introductions: If you teach prospects something valuable and ask smart questions, they'll introduce you to their network. Your first 5-10 conversations should naturally generate the next 25-100.

Chapters

00:00Introduction
02:23What motivates Oleg - people, product, then profits
03:13What People.ai does and who it serves
04:56The backstory of Semantria and cloud-based text analysis
06:44Processing 5 billion transactions per hour at Semantria
07:49Powering 90% of the social media monitoring market
08:20Building the product as a non-technical founder
09:44Selling for nine months before the product was ready
10:37Getting the first customer through consultative selling
11:15Identifying ideal customer profile by volume and revenue link
12:05Landing enterprise contracts through deep discovery
13:15Why consultative selling is really customer development
14:03Landing Twitter data processing deals
15:36Keeping enterprise prospects engaged for six to eight months
17:47No demos until the third or fourth meeting at People.ai
18:12Outbound only - no inbound marketing at either company
20:00Teaching prospects to build curiosity about your product
21:39Transitioning from Semantria to People.ai
24:44Selling Semantria to Lexalytics
25:05The $5M ARR exit and horizontal middleware lesson
27:06Building People.ai at Y Combinator
28:52Getting 100 logos in 45 days through customer development
31:44Building the first dashboard prototype in two weeks
34:15Creating social capital through smart questions
36:14Matching the right salesperson to the right prospect
37:21Fundraising and current state of People.ai
38:31Lightning round

Episode Q&A

How did Oleg Rogynskyy use consultative selling to grow Semantria to $5M ARR?

Oleg focused entirely on outbound sales with zero inbound marketing. He asked five questions before giving one answer on every call, staying in discovery mode to deeply understand prospects before ever pitching the product.

Why does People.ai ban demos until the third or fourth meeting?

Oleg believes showing a demo without deep understanding of the customer's problems leads to failure. By the third call, the sales team can position the product to address exact pain points using the prospect's own language.

How did Oleg Rogynskyy sell a product that didn't exist for nine months?

Oleg spent nine months on the phone doing consultative selling while the product was being built. He gathered customer requirements through questions and adjusted the engineering roadmap based on what he learned from each conversation.

What consultative selling SaaS tactic helped Oleg land a million-dollar Sprinklr deal?

Oleg had daily Skype conversations with Sprinklr's CTO for six to eight months. He shipped features based on their feedback without announcing them, letting the prospect discover improvements organically and building trust through responsiveness.

How did Oleg Rogynskyy get referral introductions from prospects?

By creating social capital through insightful questions and teaching prospects something new in every conversation, Oleg earned referrals. If prospects learned something valuable, they were willing to introduce him to their network.

How much preparation did Oleg do before each consultative selling call?

Oleg spent about an hour preparing for every conversation, creating 5-10 page prep documents. He read the prospect's blog posts, Twitter history, researched their previous companies, and reached out to mutual connections for personal context.

What mistake did Oleg Rogynskyy make with Semantria that led him to sell it?

Semantria was a horizontal middleware SaaS in a $100M global market - too small for venture capital. Oleg realized that without VC funding potential, his only options were to keep building a small business or exit.

How did People.ai get almost 100 logos in its first 45 days?

Oleg applied his consultative selling approach to customer development at Y Combinator. He talked to hundreds of VP Sales, built a working prototype in two weeks based on their feedback, and prospects pulled out their credit cards.

What is the "extreme listening" consultative selling SaaS approach Oleg learned from SuccessFactors?

Lars Dahlgaard at Andreessen Horowitz outlined a model where every salesperson must practice extreme listening - asking structured questions and extracting key insights from every prospect conversation before proposing solutions.

Book Recommendations

Pitch Anything

by Oren Klaff

The Hard Thing About Hard Things

by Ben Horowitz

Links

  • Omer Khan: LinkedIn | X
Full Transcript

Omer (00:11.280)
Welcome to another episode of the SaaS Podcast.
I'm your host, Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talked to Oleg Roginski, the founder and CEO of People AI.
People AI is a SaaS platform that uses artificial intelligence to help sales teams to be more effective by automatically capturing all their sales activities and then giving them clear and actionable insights.
People AI was founded in 2016 and has raised over $7 million in funding.
But back in 2010, Oleg was doing the 9 to 5 at another company when he had an idea for his first startup.
He realized there was a need for democratized cloud based text analysis.
So he left his job to bootstrap a startup called Symantria.
It took Oleg and his co founder George about nine months to build the product and to land their first customer.
And Oleg spent the majority of those nine months talking to prospective customers using a consultative selling approach.
He focused on two main things.
Number one, listening more than he was talking and two, providing his prospects with real value before even mentioning his product.
And that approach paid off.
The founders went from zero to $5 million in annual run rate in just over two and a half years.
And they did no inbound marketing.
They focused on just doing one thing well, which was outbound sales.
In this episode, you'll hear about Oleg's story and what he did to build both Symantria and People AI.
And you'll learn some awesome tactics and tips on using consultative selling with your own prospective customers.
So I hope you enjoyed the episode and that you get some actionable insights of your own.
Oleg, welcome to the show.

Oleg Rogynskyy (02:23.030)
Thank you, Amer.

Omer (02:24.870)
So let's start by asking you, like, what gets you out of bed?
What motivates you?
Is there a favorite quote that you can share with us?

Oleg Rogynskyy (02:33.190)
Yeah, absolutely.
It's the one that a lot of people read in A Hard Thing About Hard Things by Ben Horowitz.
But I really have it in front of me pretty much every day.
It says, take care of the people, the products, and only then the profits, in that order.
And that's what brings me to the office every day.
And it keeps me excited is the team I'm building first and foremost and then the product that the team is building with my help.
And then, I mean, we are far from profits, but eventually the profits that that's going to generate for the company.

Omer (03:04.260)
Yeah.
And you've been doing well on the revenue side.
So we can kind of dig into how the people in the product part has been helping you to do that.

Oleg Rogynskyy (03:12.740)
So great.

Omer (03:13.710)
So let's start by kind of setting the context and helping the audience understand a little bit more about people AI.
So what does the product do and who is it for?

Oleg Rogynskyy (03:23.230)
People AI is an enterprise SaaS company.
We started with salespeople, but now it's pretty much every customer facing role.
We connect with, go to market employees, email, calendar, phone, webex, zoom, whatever system they use for their work, pull out all the activities and then make sense out of those activities with the help of AI.
Automate all of the manual data entry across your whole revenue team, from bdrs all the way to services, customer success, et cetera, into CRM and literally guide the folks to how to do their job better based on the past experiences that them and other employees in the company have had with the customers.

Omer (04:01.450)
And so I know when I was checking out people AI, it talked about this was a tool for sales leaders.
So is this kind of more of a management tool or does it kind of help the sales guy?
Like do they enjoy using this tool as well?

Oleg Rogynskyy (04:16.130)
Yeah, absolutely, because they don't have to.
So people AI automatically takes care of all the tedious work that salespeople have to do by entering stuff in their salesforce, keeping their notes, all that stuff.
And so we literally free up every time we've gone into a customer install.
We free up about 20% of time for every salesperson from the most annoying work.
So by not having to do anything, they actually end up loving us.
And then on top of that, there is an interface that allows them to get better at their work.
So surfaces, insights and best next actions for the salespeople to drive best results from the limited amount of time they have.

Omer (04:56.730)
Cool.
So I want to talk more about how you built that business, but before we do that, I want to go back a few years and spent some time talking about your previous startup, which was Symmetria, and you bootstrapped that business and then went on to sell it several years later.
So I kind of want to dig into that because I think in many ways that is a big part of the story and how you got to building people AI.
Tell me, like what was that product about and how did you come up with the idea for it?

Oleg Rogynskyy (05:28.650)
Yeah, absolutely.
So before I started Symantria, I was working for a company called Lexalytics and before that actually at Einstein, which were both in a similar space.
It was in natural language processing space.
And both companies were selling on premises, hardware and software for natural language processing.
So you basically buy a box and you send some text to the box and then some kind of output or metadata comes back from the box and you do something with it.
While working for both of those companies, we were selling very chunky deals.
I mean, half a million dollars, million dollar deals here and there.
We were turning down hundreds, if not thousands of individual contributors, students, startups, small companies, or companies who cannot afford to spend a million dollars on a feature which is natural language processing.
And so I noticed by working at those two companies that there is a strong demand for natural language processing and sentiment analysis delivered as SaaS.
And so when I decided to start Symantria, I left Lex analytics and we built the world's first scalable cloud based sentiment analysis API that allows you to literally put in your credit card and send a stream of content to the API and get it processed.
And it doesn't matter Whether you have 10 tweets or 10 billion tweets, the system can handle it.

Omer (06:44.640)
So give me an example of kind of the sentiment analysis that you would do.
And I think I read somewhere that like a Yelp comment would be one example of what was being processed through Symmetria.

Oleg Rogynskyy (06:55.960)
Towards the end of my tenure at Symantria, we're processing over 5 billion transactions an hour.
We were scanning all of the new content generated across the whole Internet in real time, many times over.
And so that's the magnitude the actual processing results.
I mean, most of the content was Twitter reviews, comments like, Yelp is a good example of that.
Survey results.
So anything that has text and anything where you have to turn text into structured data for further analysis, for training, machine learning models, etc.
So use cases would be.
The biggest use cases we had was social media monitoring.
We literally powered over 90% of social media monitoring market.
So these are companies like in Salesforce, is there Sprinklr, spreadfast, hootsuite, all the folks that scan what is being said online and tell you what's been mentioned about your brand, what are the trends, are they positive and negative, etc.

Omer (07:49.650)
Those products you mentioned were all using Symentria.

Oleg Rogynskyy (07:52.580)
Yeah.

Omer (07:53.460)
Wow, that's really surprising.
I'd never heard of symmetry before, but now you start to peel back the layers and it's like, wow, probably most of us listening to this have probably interacted with symmetry at some point without even knowing about it.

Oleg Rogynskyy (08:08.260)
Probably like within the past hour.

Omer (08:10.740)
Yeah.
Okay, so you saw this opportunity and how did you go about Building the product.
You're not a developer by background, right?

Oleg Rogynskyy (08:20.070)
Yeah, no, I'm not a technical founder.
I saw the idea.
I had been in sales for about eight, nine years before then, and so my kind of sense got.
And my marketing got.
Let me see the opportunity around building a business.
But when it came to building it itself, I literally found my CTO online.
It was not a dating website, but it was kind of through a few connections.
I found George, and he had found a few engineers that we brought on board.
I was bootstrapping at times, so it was all my credit cards, and we started building.
Took us about nine months to get to the first working version of the product.
In fact, there is a connection there between what I do now and what I did then.
The initial version of the product was focused not on general sentiment analysis, but just on sentiment analysis of your notes in Salesforce to the salesperson.
You're putting in a bunch of notes into Salesforce, and then we would do sentiment and put the sentiment data back into Salesforce.
It turns out that was too early for the market.
And so we unplugged Salesforce and just turned it into a general API.
But, yeah, spent about nine months building the first version.
Then first customer showed up and started paying us good dollars.
We realized there is a market there, and we kept on refining the SaaS product until it became what people actually wanted, which is something I learned much later from Y Combinator.
That's the only thing that matters.
Build something people want.

Omer (09:44.970)
And so how were you figuring out what to build in those nine months?
Was this just based on your experience and what you and George kind of felt like the product should do, or were you trying to get feedback from the market at the same time?

Oleg Rogynskyy (09:58.490)
Yeah, I mean, most of my time was spent selling something that didn't exist back then.
I was literally on the phone trying to sell the product we were yet to build.
And from those conversations, I was gathering more and more information about what people want and changing the course or correcting the course of my engineering team to stay on track with what I was learning.
Full transparency.
That's probably the most annoying part of building a company for any engineer, because your feature set and your roadmap is changing five times a week.
But then if you get through that, suddenly you end up with a product people keep on using, which is great.

Omer (10:37.260)
So you were selling for nine months before you got your first customer, or did you get your first customer because it took you nine months to build the product?

Oleg Rogynskyy (10:45.180)
It's kind of both.
So I was selling for nine months and we got a few customers initially that weren't exactly our ideal customer profile.
But it only took us to close them and try to service them, to learn that they are not the perfect profile for us.
However, by the time we released the first working version of the product and stopped kind of filling in manually for it, we had a few customers where it was just going really well.
And so we knew we need to focus there.

Omer (11:15.740)
Who was your focus?
Like, who did you decide were the ideal customers for this API?

Oleg Rogynskyy (11:21.820)
We decided that these were companies that had a lot of text.
The volume of this text was unpredictable.
So, for example, Twitter.
I remember the day when Michael Jackson passed away.
Twitter volumes went 100x for an hour.
And there is no way, if you had a hardware box with limitation, you could have handled that.
And so we needed people who do not know what the volume is going to be tomorrow, and also companies that could place a dollar value on processing of this tax.
So someone who can build a product on top of it and charge more for it, or who could sell a service based on sentiment analysis.
If there is a direct link between revenue and the feature that they were building based on our technology, then we could easily justify ROI and drive expansion.

Omer (12:05.600)
And what kind of conversations were you having when you were kind of picking up the phone and talking to people?
Because the product is still evolving.
It's not like you can clearly say, hey, here's the product.
These are the benefits, these are the features.
How were you kind of figuring out?
Like, how were you kind of articulating what the product was while it was still being evolved, it kind of still being developed and figured out I had

Oleg Rogynskyy (12:29.290)
a rule for myself.
I literally would stand near a whiteboard and put like four sticks vertically, one across.
I was not allowing myself to make a statement before I ask five questions on every phone call like that.

Omer (12:42.250)
What were those five questions?

Oleg Rogynskyy (12:43.530)
No, just like, what are you currently doing with the data?
What do you use it for?
How are you monetizing it?
What would you like to do with it?
Where do you store it?
How do you store it?
How much of it do you get per week, per month?
So if you train yourself, you keep on asking questions and you keep on learning more and more about people you're talking to.
But the idea is you should ask five questions before you give one answer, and then you ask five questions again, you give one answer.
And so if you are staying in the discovery mode like that, your learning rate will be much, much higher.

Omer (13:15.310)
I mean, in many ways, this doesn't sound like a sales conversation that many of us would kind of expect.
Right.
In terms of it didn't sound like there was much kind of pitching of your product going on.
You were just kind of just gathering data, you were doing research.
In many ways, it was kind of like just doing customer development.

Oleg Rogynskyy (13:34.670)
Absolutely.
That's what drove us to success, is the fact that we knew our customers really well and we were building the product to what the customers wanted.
But at the same time, if you have a first call when you ask a lot of questions and you actually writing everything down and you're remembering it, next call you have with them, you come back, you sound 100 times more relevant because you're speaking their language, you're using their own phrases.
And your product, the way you're positioning the product is to address exactly the pain points that they have told you

Omer (14:03.720)
before about what did it take to land a customer like Twitter and for them to want to use a third party product like Symmetria to do this kind of sentiment analysis?

Oleg Rogynskyy (14:15.460)
Yeah.
So I want to stand corrected.
Twitter directly was not a customer, but everybody who was buying Twitter data because Twitter was never selling, processing data themselves, they were just selling it got it.
So everybody who was buying Twitter data from Twitter and then processing it for a customer.
Lending someone of, let's say, sprinkler size was a lot of work.
It took about six to eight months of just talking to the engineering and letting them play with our APIs and hearing from them.
And also what was really important is iterating the product fast enough for them to notice that you are listening.
Was what it took to land the first contract.
I literally had their CTO on Skype with me and we were talking every day, every second day, every time there was a problem, he would Skype me.
Every time I had an idea, I would run it by him.
And then what was interesting is I was never telling them when we ship something, but they were learning about it by using the product and then they realized there is a loop.
You tell Symantria an idea and then two weeks later this idea comes to fruition.
They weren't seeing anything like that from any other vendors.
And so six, eight months later, they knew they could trust us to build the product that works for them and that we would be listening.
Not just in the beginning, but over time.

Omer (15:36.270)
How did you keep them engaged for six to eight months to kind of a typical situation would be is somebody kind of gets their foot in the door, starts to have a conversation with an Enterprise type customer maybe does a demo, their team kind of plays around with it a little bit.
But to have somebody engage and continuously over this sort of six to eight month period using your product, learning about it, giving you feedback, what were you doing to kind of keep that level of engagement from the potential customer?

Oleg Rogynskyy (16:09.880)
One piece about my background to understand is I had been doing enterprise sales for a while and relationship building as well as kind of going really deep into your customer's problems is a bit of a second nature.
In fact, at People AI today we're not allowed to show demos until a third or fourth phone call or meeting that we do with the customer.
Just because there's no way you can show a demo without having a deep understanding of what the customer wants and be successful.
And so going back to Symantria days, that was that.
I mean, I did show them the product probably after three or four meetings and they start playing with it.
But what you got to do to lend a large contract, the deal I'm talking about with Sprinkler was over a million dollars.
To lend a large contract like that, you got to keep on uncovering additional use cases, you got to keep on uncovering additional customer or their customer needs.
And you got to keep on uncovering corporate initiatives, both official and unofficial, and find ways to tie your product to them or tie those to your product.
So if you're going deep and wide, you're going to find more and more people who you need to sell on.
And the more people you sell on your product within the company, the more budgets you can tap into, the more understanding of the value that you're delivering to them you get, the more value you can in the end deliver and then turn on not just the product sale, but consultative sale, where you use your product knowledge to help them solve not just specific feature requests, but overall business needs.

Omer (17:47.270)
And so after nine months, you've got the product out there, you've got, you've landed your first customer.
I'm kind of curious about this process you talked about with the phone calls and even with people that they can't show the demo until the third or the fourth phone call.
So were you doing something similar with kind of this product and what would typically happen on the first and second calls?
Like what were your goals on those first two calls before you even went to the demo?

Oleg Rogynskyy (18:12.730)
Yeah, I mean, another piece that we don't do here at People AI and we didn't do much at Symantria back in the day is we wouldn't do inbound sales and marketing, it was only outbound.
And so when you only do outbound sales, you actually have to pre qualify who you're calling or who you're reaching out to understand their business, at least on the surface, what's available publicly.
And, and reach out with a very targeted message, ideally with an introduction from a trusted person that says, hey, these guys understand your business.
You should talk to them.
My favorite question when I get on a phone call like that is, hey, Omer, why are we here?
Your time is very valuable.
You decided to spend an hour of your time on the phone with a vendor like us for a cold call.
And obviously we had a bit of conversation via email before.
What caught your attention?
What made you invest an hour of your time in talking to us?
If you ask the question up front without showing a demo or telling them anything about what you do, what the person's gonna tell you is, hey, we have this initiative.
I was thinking that we have a lot of text in this initiative.
Maybe you could help us understand this text.
And I'm hoping I can get X, Y and Z out of it.
And so if the beginning of your first conversation, you're armed with all this information, you truly listen, the next thing you're going to say is, oh, yeah, you know what that initiative sounds like?
5 initiatives we've sold for our customers previously.
And here is examples, here is testimonials, here is how we help them out.
Here is the outcomes.
And from there, instantly you are in collective solution mode, instead of them being defensive and you trying to shove something down their throat.

Omer (20:00.180)
So this is kind of, I guess, goes back to what you called it earlier, like consultative selling.
Right.
In terms of you're just having the conversation in terms of trying, number one, trying to understand their problem, and number two, giving them examples or case studies or ideas on how to solve that problem.
But your product hasn't really come into the conversation yet.

Oleg Rogynskyy (20:22.420)
Yeah.
And you know what?
Tell me one thing, and that's a question for you.
If you meet with a person who seems to be very smart and they're asking questions that make you think through your problems deeply and maybe realize things you haven't realized when someone is guiding your thinking with their questions, would you become curious about how they came up with those questions and how can they help you or how can you tap more into the expertise?
Of course you would, right?

Omer (20:50.890)
Yeah, totally.
And I think it would also very quickly switch me from, I'm going to talk to someone who is kind of going to come and pitch me A product to.
It kind of sounds like I'm just talking to somebody who's interested in brainstorming this problem with me.

Oleg Rogynskyy (21:09.060)
Exactly.
And also because they've supposedly they've solved similar problems before, they come from a position of an expert in solving such a problem.
And so you actually, the goal of my conversations like that, from my perspective, are to teach the prospect something they didn't know before.
And you know what?
When you get on a call with vendor, and the first 30 minutes of that conversation, they made you think about your blind spots, and then you learned a bunch of things, you'll want to have a second call.

Omer (21:39.940)
Those are great tips.
And then so in terms of growth and acquiring more customers, for Symmetry, it was all outbound.

Oleg Rogynskyy (21:49.710)
Yeah.

Omer (21:50.910)
And like, how long were you doing that before you hired somebody to kind of help with the sales?

Oleg Rogynskyy (21:55.790)
Probably first year, year and a half.
And then I got some salespeople.
But what I learned at Symmetry, and I failed at that at Symmetry, but I think I'm succeeding at that at people AI is how can you train other salespeople who haven't been trained on the approach I just described to you?
How can you make every salesperson, you have an expert in the field that is very curious and inquisitive about how customers solve these problems?
And basically, the salespeople that are able to do the same kind of customer development work as a part of the sales process.

Omer (22:29.700)
So that's interesting because a lot of the times we kind of hear, well, you know, especially in the early stage, the founder is kind of like the best salesperson, because you kind of have been probably the driver of the vision, you know, the product the best.
You're kind of probably the most passionate about it.
And so you can kind of articulate that and convey that sort of enthusiasm with potential customers.
But what we've just talked about suggests, well, yeah, that stuff is important and.
But later.
But the initial conversations is really nothing to do with.
With the product.
It's about building that sort of mindset that we just talked about in terms of asking smart questions, digging deeper into what problems people are having, helping to teach them something without kind of going into pitch mode.
How did you learn how to get that sort of mindset into people and kind of what are some of the challenges that somebody who maybe is in a similar situation should be thinking about?

Oleg Rogynskyy (23:30.310)
So initially, I came up with this a little bit intuitively, but when I moved to Silicon Valley in 2014, I ran across a partner at recent Horowitz, Lars Dahlgaard.
I think he's no longer there, but he used to be the founder of Success Factors, and he has one blog post that really stuck with me because it clearly outlines the model I've just shared with you.
And so that blog post is called use your ears.
And the favorite quote I have from that blog post that I'll never forget is, you have two ears and only one mouth for a reason.
You should be listening twice as much as you're talking.

Omer (24:07.110)
Love it.

Oleg Rogynskyy (24:07.990)
Yeah.
And so that blog post is really long.
It's probably 10, 15 pages, but it's brilliant.
And it literally outlines how Lars forced every salesperson at SuccessFactors to do what he calls extreme listening.
There was a set of questions, a set of ideas that every salesperson had to get out from every conversation they had with their prospects.
And so that's what I took very dearly to my heart and have started thinking around it and also building both our product and our team at PeopleAI now around listening.

Omer (24:44.030)
So you went on to sell Symmetria a few years ago.
I don't have the exact time.
It was like, 2014, June 30, 2014.

Oleg Rogynskyy (24:57.350)
It was literally three years ago.
Or is it four now?

Omer (25:02.070)
Yeah.
How much money had you raised by then?
How much were you doing in terms of revenue?

Oleg Rogynskyy (25:05.990)
We're doing around $5 million a year.

Omer (25:09.670)
You actually ended up selling it to Lexa.
How do you pronounce it?

Oleg Rogynskyy (25:13.990)
Lexalytics.

Omer (25:14.630)
Yeah, Lexalytics.
Right.
Which was the company that you were working for before you kind of went out.
So, like, how did that happen?
How did that sale come about?

Oleg Rogynskyy (25:22.060)
Well, they were in the same space.
They were selling on prem sentiment and NLP technology while I was selling SaaS.
And if in the beginning, when we kind of convert, when I departed from lex analytics, on prem and SaaS were very different customer profiles.
There were big companies that would never do SaaS, and there were small companies that couldn't afford on prem.
We by three, four years later, those two worlds started converging.
Big companies started embracing cloud, and small companies started understanding when they need to deploy on premise versus not.
And so it really made sense for Lexalytics to acquire Symantria to add a cloud solution to their product line.
And at the same time, in your prep flow for this podcast, I found a very interesting question, which is, what was my biggest mistake?
And so this is when I realized they had made a big mistake.
Not about selling the company, but turns out that if you're building a horizontal SaaS play, that is middleware in a Small market, you will not be able to raise venture funding, period.
And so there was a choice of continuous building a small business exit or exit.
There was no third option.

Omer (26:38.640)
So, okay, that was the other question I was going to ask you is whether you had raised any money.
And we know the answer.

Oleg Rogynskyy (26:44.000)
Yeah, it was a full bootstrap.
But if you're middleware and your market is not billions and billions of dollars and turns out that sentiment analysis market is rather small, at that time it was about $100 million a year globally.
You just don't have enough market to capture to become an interesting business for venture capital capital investors to get excited about.

Omer (27:06.000)
So you went from, I guess like a three, three and a half years from launching Symmetria, building out the product, getting your first customer, and then basically pretty quickly getting to $5 million.
ARR.
After that.
It sounds like things went really well.
Like it was really easy to do that.
Like, what were some of the kind of the tough moments or maybe a tough moment that you can kind of share with us?

Oleg Rogynskyy (27:35.480)
Well, I got in a pretty bad accident probably three months into starting Symantrea and ended up in the hospital on crutches or in a wheelchair for about six months after.
So basically the part of the story where I was telling you I was on the phone talking with customers, I was also not able to walk.
That's why that was the only thing I could be doing at the time.
And so the tough moment was the onstar of the business was pretty tough from my personal health standpoint, but also it allowed me to completely focus on the business.
That was the only thing that would distract me from kind of the personal situation.
But then once I persevered and I got back to being able to walk and all that stuff, it really, looking back, I realized that that's what the absolute focus that I got by not being able to do anything else physically was.
What launched Symantria into stratosphere so quickly?

Omer (28:29.450)
Wow, that's a great story.
And then so once the Symmentry was acquired, you were at Lexalytics for about a year.
And I guess after the acquisition, it was probably about two years before you went out and started to decide to build people AI.
How did the idea of a people AI come about?

Oleg Rogynskyy (28:52.340)
It goes back to the initial Symmetria.
I was like, wow, back in the day we wanted to process content that salespeople put in Salesforce.
And it was too early.
People weren't thinking about that back yet.
And then I started thinking about my experience Selling.
And I realized that one thing I dreaded the most was doing the work twice.
First you talk to a customer, and then you log that data into Salesforce.
You have to literally type it up or do a bunch of clicks without actual purpose from my perspective as a salesperson.
And so we got into Y Combinator rather quickly, just because they knew that the direction is interesting.
And I kind of had a track record of building a company, so they trusted me.
And one thing they really pushed me to do is extensive customer development.
And so I ended up going and talking to 100 VP sales or a few hundred salespeople in a very short period of time.
And I realized I wasn't the only one who was hating data entry, who was hating doing the work twice.
But also I wasn't the only one who was lacking data about my sales team to make them better.
Reliable data is really hard to comply with in a sales team because it's all based on manual data entry.
And so I knew there was something there.
We started building.
We started listening to customers again.
Initially, we built a very simple dashboard that literally tells you what your sales team is doing today in real time.
You don't have to run reports or ask people.
You just pull up a dashboard and see what's happening.
Turns out that that was really interesting.
And we got almost 100 logos in the first 45 days right before demo day at Y Combinator to start using the product.
And that's what led to our Series A.
And then we started listening to customers more and more and really realized that the larger the company you're working with, the more they need this kind of technology.
And so we moved to upmarket really quickly.
We got into my comfort zone of very large deals, and that's where things start cranking very well.

Omer (30:52.770)
The dashboard that you described, like, what was it doing on the back end?
Like, were you just kind of hooking into Salesforce?

Oleg Rogynskyy (31:00.930)
We were hooking into Salesforce.
Email server, Calendar, phone systems, PBXs, dropboxes, DocuSigns of the world, et cetera.
Basically, anything that a salesperson is using for their work, it would pull out all the activity and then make sense out of that activity.

Omer (31:18.780)
And how long did it take to build that dashboard?

Oleg Rogynskyy (31:22.540)
Two weeks.
For the first prototype.
We had tried something else before, and it wasn't working.
And then when I realized I had an aha moment that this is where we should go, we literally used the backend from the previous product, which was kind of in this direction, and just rebuild the front end and it started working more or less, and then over time, we optimize it and rebuilt it to serve this specific purpose here.

Omer (31:44.720)
And in terms of getting people to use the dashboard, were you just going back to these VP of Sales that you had kind of been doing customer development with and just introduced them to the dashboard?
Is that how you kind of quickly got people using that product?

Oleg Rogynskyy (32:00.000)
Absolutely.
I mean, first I reached out to 1 VP sales and asked them questions, and turns out that if you talk to someone, ask them really smart questions, hear them out, and then two weeks later you come back with a working prototype of exactly what they wanted, but not necessarily even told you, you know what they're going to do, they're going to pull out credit cards.

Omer (32:21.420)
How are you getting in front of these people?
Obviously, what we were kind of learning from this experience is sending an email or trying to get a call scheduled or a meeting scheduled.
And talking about your product is not a good way to kind of go.
But, like, typically, like, what would you say to try and get some time with these people?

Oleg Rogynskyy (32:42.470)
Going back to our original conversation about adding value, even on the first phone call, getting first five or 10 people is not hard.
Anybody should be able to do that.
And if you can't get your first 10 VP sales on the phone trying really hard, you probably shouldn't be building a company.
But then as you're talking to the first five, if you did well in your conversation, you taught them something and the questions you asked them were actually interesting and the conversation was insightful.
One thing you can do is you can say, hey, who should I have a similar conversation with in your network?
And if they like talking to you and they learn something, they'll say, oh, of course, go talk to Bob and Mike and Jill.
They will give you some more insight as well.
And so the first five, 10 conversations turned into first 25, then they turned into next 75, 100, and so on and so on.
So you just need to be listening, you need to be smart and asking the right questions.
And you also need to be taking very extensive notes of every conversation.
In fact, since I was doing customer development, I will ask them up front, hey, do you mind if I record this conversation?
And I would literally have a recording, and then I would re listen to it a few times, transcribe it, turn it into notes, feel the pain of the future product I'm going to build.
But also just hear the language, hear the intonation, hear the annoyance when they were talking about specific problems.
And then that led me to really deeply understand them and come back to them with a solution that was solving something that wasn't even on the surface.

Omer (34:15.689)
That's really interesting.
I think this idea of asking them if there's somebody else in their network that you should talk to or be interested in, this is great because number one, I think people like to help if they can.
And secondly, if you're being, you're asking smart questions, you're kind of helping them kind of think more deeply about their problems.
You're not just pitching then I think people are going to be even more comfortable recommending you to somebody that they know.
Right.
As opposed to, well, this guy's just going to go and pitch them and annoy them.
So I'm not going to tell them about anybody that I know.

Oleg Rogynskyy (34:50.689)
The a good way to think about this is if you are creating social capital for them, they'll introduce you.
If you're burning their social capital, they will block you.
So you need to sell them not on your product but on the fact that by introducing you to their network you will help them create more social capital.
That's the key to success there.
And the way to get there to persuade them that you're going to give them more social capital is homework.
I literally would spend about an hour preparing for every conversation I had early on average prep talk I would have would be 5, 10 pages long.
I would read every blog post this person had ever written.
I would read their Twitter for the past year or two.
I would go google them and see what other people say about them.
I would research companies they used to work at.
I would research every connection in common I had with them and even sometimes reach out to those connections in common and ask for back channel reference and maybe some personal notes.
Maybe this person likes golf or basketball, etc.
Etc.
Etc.
So I would come into the conversation knowing them as well as anyone.
They would feel like I'm part of their network already.
I would know connections in common.
I would have back channel.
I would know where they came from, where they grew up, which school they went to, what they studied and all that stuff.
I mean it's all public.

Omer (36:14.010)
That is great.
And just the stuff you rolled out, I think in terms of that's a great checklist for anyone who's having any kind of conversation with enterprise type customer and in many ways any potential customer that you're having with any sort of B2B.
There are a lot of these things that you can do.

Oleg Rogynskyy (36:29.740)
Yeah, I mean here's an example I had last week which was really interesting.
We Were meeting with a CRO of a massive technology company.
We're talking like over $100 billion to technology company.
And I just googled it and I found out on the CRO's public Facebook that he's a basketball coach on his free time.
And so what I did from there, I have a number of salespeople.
One of my salespeople is a basketball player.
Tall, well built guy who used to coach basketball and who used to play and now he's coaching.
So guess what?
I picked the right salesperson for the right company.
They hit it off awesome.

Omer (37:09.830)
I love that.

Oleg Rogynskyy (37:10.390)
It's all homework.

Omer (37:11.510)
So like, where are you with people at AI right now?
Because you recently raised, you've raised about $7 million to date with that business, right?

Oleg Rogynskyy (37:21.660)
We've raised more, but we are preferring not to publicize some of the fundraising events we've had.

Omer (37:27.500)
So more than $7 million.
And so kind of like what stage is the business at?
I mean, can you kind of share any revenue numbers and kind of like, you know, size of team, like what's going on with the business?

Oleg Rogynskyy (37:38.380)
Yeah, so we have 55 people going to 100, doing well, working with large enterprise.
There is a significant number of public companies that rely on our software today.
Unfortunately, I cannot disclose revenue numbers and fundraising numbers.
That's in flight.
But the business is growing nicely.
Going back to the original quote, I mentioned that people are first.
We're really focused right now on hiring the best people for every job that we can get.
And so the main question that I ask when I come into the interview before we make an offer to a candidate is, is this person going to be legendary at this job?
And if the answer is no, we should keep on looking.

Omer (38:19.460)
Love it.
All right, it's time for us to wrap up and get onto the lightning round.
So I'm going to ask you seven questions.
Just try to answer them as quickly as you can.

Oleg Rogynskyy (38:31.620)
Okay?
Ready?
Yeah.

Omer (38:33.540)
What's the best piece of business advice you've ever received?

Oleg Rogynskyy (38:37.220)
Write out all of the learnings you got from a first customer.
Call customer discovery on one page and share that one page with a customer.
Very often they'll actually go and correct your perception to how they see it.
And that's going to give you a roadmap to talk to them further.

Omer (38:54.310)
What book would you recommend to our audience and why?

Oleg Rogynskyy (38:57.350)
The Hard thing about Hard Things.
Ben Horowitz really nailed the ups and downs of entrepreneur's life there.
Another one that I actually recommend is Pitch.
Anything.
Really helped understand the room dynamics when you are in a, in a high value business meeting.

Omer (39:13.710)
What's one attribute or characteristic in your mind of a successful entrepreneur?

Oleg Rogynskyy (39:18.030)
It's great.

Omer (39:20.430)
What's your favorite personal productivity tool or habit?

Oleg Rogynskyy (39:24.990)
It's front app and the reason why I use it for my email is because you can delegate in a very transparent way.
You can delegate emails in a transparent way or you can discuss emails in a thread without forwarding them.
So in our company, nobody forwards emails, which is amazing.
And in terms of habit, it's snoozing emails.
If you want a reminder about something, you snooze an email about that for a couple of weeks and then it comes back and you go and follow up on that with the customer or the prospect.
I literally heard a rumor within my company that I have perfect memory because I never forget anything and it's all thanks to snoozing emails.

Omer (40:01.420)
You know, isn't that such a great feature that it seems to have become a lot more common in the last year or two that you see it in pretty much every email app?
But yeah, it's kind of certainly changed the way that I look at email.
What's a new or crazy business idea you'd love to pursue if you had the extra time?

Oleg Rogynskyy (40:17.520)
It's an interesting one.
So I mentioned that the best characteristic I learned about successful entrepreneurs is grit.
I would love to find a way to quantify grit of a human.
How much grit do they have?
I even bought a domain name called Grit Metrics for that purpose.

Omer (40:33.290)
Wow.
Wow.
That's pretty mind blowing.
Just think about how you would do that.
Leave them on an island.
I don't know.

Oleg Rogynskyy (40:41.930)
There is many ways to do that, but understanding how much grit someone has leads right away into how much integrity they have and so on and so on.
It's an interesting direction.

Omer (40:51.530)
Yeah.
All right.
What's an interesting or fun fact about you that most people don't know?

Oleg Rogynskyy (40:57.700)
I live in Palo Alto right now.
It's the first small town I ever lived in.
I've always lived in very large cities, so it's an interesting transition for me.

Omer (41:06.260)
And finally, what's one of your most important passions outside of your work?

Oleg Rogynskyy (41:10.660)
It's still related to work.
I love helping people develop.
So within Y Combinator network, I coach a few startups and just in my personal network, there's people coming to me for help with sales process, marketing process, fundraising, et cetera.
And I really enjoy it.

Omer (41:30.050)
Awesome, Oleg, thank you.
It's been a pleasure talking to you.
If people want to check out people AI, they can go to People AI.
And if folks want to get in touch with you, what's the best way for them to do that?

Oleg Rogynskyy (41:44.370)
The best way to reach me is to message me on LinkedIn.
I check it daily, so we'll be glad to help out folks if they have any questions or I need help with my sales process.

Omer (41:54.780)
Awesome.
And I'll include a link to your LinkedIn profile in the show notes so people can get to that easily.
Thanks again.
I kind of really appreciate you taking the time to join me and sharing both your story about Symmetria and what you're doing with people, but also a ton of really useful advice on how to approach outbound sales.
And you came up with a lot of specific things in terms of like how to have good conversations with people and basically kind of become just a lot more effective at selling, I guess, without selling.
Right.
And so I really love all that sort of information you shared with us and thank you for that.
And I wish you all of the best with your future success with People AI.

Oleg Rogynskyy (42:42.680)
Thank you, Omar.
This is a pleasure.

Omer (42:44.840)
Awesome.
Cheers.

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