SaaS Breakthrough – Featuring Rajiv Nathan

demio saas breakthrough featuring rajiv nathanAbout Rajiv Nathan:

Rajiv “RajNATION” Nathan is the founder of Startup Hypeman and is known as the Heavyweight Champ of storytelling.

Rajiv helps SaaS startups not suck at how they pitch and tell their story so they STAND OUT to customers and investors, and STAND APART from competitors.

His work has been featured in Inc, Forbes, Huffington Post, and more, and he’s partnered with accelerators across the U.S.. When he’s not doing that you can find him teaching yoga, or making music as a rap artist.

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Show Notes:
Build Out Your Pitch, Message, Story to Stand Out
Finding the Way Towards SaaS
The Concept of Problem Market Fit
Empathy vs Product Features
Creating Empathy: The Superhero Strategy Framework
The "Que PASA" Formula
The Elevator Pitch as The Movie Trailer
Borrowing From Entertainment to Make Business Communication Sexier
Thinking Like An Entertainer and Less Like an Entrepreneur
Create Thoughtful Messaging for Your Particular Audience
A Whole Day Rollout Meeting
Applying The X to Y Paradox On Outbound Email Campaigns
Sales Enablement At An Earlier stage, Network Effects and Diversity
Lightning Questions

Hello and welcome to the SaaS Breakthrough podcast. Thank you so much for jumping on with me today. I'm really excited to have you on, talk about Startup Hypeman and everything cool you're doing over at your business. How you doing today?
Rajiv [03:23]:
I am doing fantastic. As they say in the radio world, a longtime listener, first-time caller.
David [03:27]:
I like that. That's awesome. Well, let get up to speed. Talk about Startup Hypeman. What is going on with that? When was it founded? Who are the customers and what are you guys doing over there?
Rajiv [03:38]:
Yeah. So, I think probably the best way I can explain it especially given some of the things one of getting into is just to give you like my elevator pitch, right? I think it would probably be a good starting point. So, really what it stems around is I talk to founders and CEOs pretty much every day who will straight-up tell me “Hey man, we suck at telling our story” and it's typically that, if it's not directly that, it's something that sounds similar to that.
But that sucking at telling the story affects their demo closing rates, their lead quality and their ability to get ever on the same page internally. So, my job is to help them not suck and what I do is use a unique combination of branding and sales and entertainment based principles to work side-by-side with the company and build out their pitch, their message, their story to make them stand out to customers and investors and stand apart from competitors.
So, I've been doing this since 2017 and really the way this kind of like comes together as far as like a service offering is I work with a company and build out a playbook that ultimately gets integrated into their sales and marketing processes. So, Startup Hypeman works with companies in, I would say three different tiers or stages. Tier 1 would be the SaaS startup that either like recently raised a million or more or if they bootstrap, they've crossed a million dollars in ARR and now, they're in this like 12 to 18 months scale or die window.
And at this point, they're obsessed over two things. Hiring the right people and getting their messaging down. And that's where I come in as on that second part. Tier 2 is the earlier stage SaaS hovering around let's say like 20k MRR or somewhere near there. And these are the ones who are looking to push past product market fit mode and prove to investors they have an investable business on hand.
And then, tier 3 would be earlier stage startups and this is really any startup looking to raise capital, so they're the ones that typically, they're too technical in their pitch or just don't do a good enough job articulating the vision and I will work with them to build out a really sound investor pitch. What you'll notice is that I gave you three different tiers but the uniting factor amongst those tiers is the dire need for a pitch, a message and a story.
David [06:01]:
Yeah. That makes sense. You've really honed in on the pin point and how did you find that pin point? What were you doing beforehand that led you to launch this kind of agency or this type of service? And how did you initially decide to work within the SaaS space to go with that problem?
Rajiv [06:18]:
Yeah. I feel like it's like sort of a long winding road to how I got here and if you were to tell me like five years ago, this is what I would be doing, I would have said “Yeah, right” but I mean It’s a stuff I really enjoy. I'm definitely passionate about it, I actually never thought this is where I'd end up. So, prior to this, I had a separate business with a partner which was actually around personal brand development.
And what we were best at with that was around developing elevator pitches for individuals and that could be like for CEOs, for entrepreneurs or even like people who are looking for like job interviews and looking to answer that “Tell me about yourself” question and so it's just so through doing that, I networked a lot with other entrepreneurs here in the Chicago. Entrepreneurship and startup scene and I got in contact with a group called Bunker Labs, specifically like the CEO of Bunker Labs, his name is Todd Connor.
So, he had kind of observed from afar and seen me up close through some like events do this elevator pitch work and that previous business I had which is called Idea Lemon, did it for two years. Halfway through year two is when we saw that the business model just isn't working so what we realized is we have to shut this down and then almost serendipitously, when we had those conversations is when Todd Conner from bunker labs reached out to me and he said “Hey, I know you're good at this pitch stuff’.
We had a cohort come in through our last batch and they just kind of, for lack of a better word, they shot the bed on their pitch day. Said “Would you be interested in like working with our next cohort and get their pitches in order?” and I was like “Okay. Sure I can do that”. And then, I hung up the phone and I was like okay what do you do for a meeting? I started Google searching like what goes on in an investor pitch. So, in doing some research I was like ok I get the framework here.
I can understand how this operates and having my own just like base storytelling knowledge, I was able to like meld the two together and Bunker Labs brought me in on this like small outside consulting contract work with their cohort and actually, initially where this got started was in strictly working with startups on their investor pitch. And that's how I got the ball rolling with this in the first place.
Over time, I found my way towards SaaS, I think because of where I had previously worked at a digital agency that went towards a SaaS model, during the later years I was there. and then also I think just for whatever reason, I just started to naturally grasp the SaaS sales process particularly B2B and then one of my clients ended up wanting help for both investors relations but also on their sales and marketing side and they were a SaaS company. And that's kind of what set it off on the SaaS side.
David [09:24]:
It's funny how that journey kind of takes you sometimes, just because of past experience, into a marketplace that you never thought you would be in. I mean you're in personal development before that. By the way, I love your different company names. I think you do a great job picking names. They're fantastic.
Rajiv [09:39]:
You wouldn't believe by the way with the Idea Lemon, how long we spent thinking of a name and I would say an advice to an early founder. Just figure out your product, you can figure out the name later. We spent way too much time on the name and not the product.
David [09:34]:
A lot of people do that with a logo too. They spend so much time on the small stuff but yeah, definitely spend the time on the product. Listen you're saying a word that I think is so critically important and a lot of like digital marketing, internet marketing, that whole space talks about storytelling a lot with copywriting.
And this is funny that in the SaaS industry, we talk about messaging a lot but I don't really hear the word storytelling often and I think everyone in SaaS that wants to improve their messaging, I think we know how important it is and there have been people that have come on and literally talked about “Hey. The past six months, we've just been trying to unify messaging. We're trying to unify our company just to get everyone together”.
It's such a hard thing with business and it sounds like you've had a really good background. You've done storytelling in different areas, you understand the power of copywriting and messaging. So, when you talk to these SaaS companies in the different tiers that you talk to them, what does it take to craft the perfect message like how do you actually talk about that? Are you talking purely boiling it down to figuring out their story and building up from them or what goes into that?
Rajiv [10:58]:
Yeah. So, it's really around when I talk about like messaging for a company, what I'm looking at is what's your positioning? What's your elevator pitch? What's your brand story and then, are you using a sales deck if you have a B2B sales product and how effective is that deck? So, when we look about like how do you actually go about crafting this stuff? To me, what it starts with and I think this is a term that, it's something I was like doing but I didn't have the term for it until someone who came on to my podcast mentioned it.
And she was a guest. Her name is Humaira Ahmed, she's the founder of a networking app for women called Locelle but she used the phrase ‘problem market fit’. Now, everyone's familiar with the phrase product market fit and I actually think this is where a lot of companies go wrong is they're so obsessed with product market fit that many of them try to shoehorn product. They try to shoehorn it to make the fit instead of it being a natural fit.
So, if you think about this concept of problem market fit, if you focus on this aspect, it is going to make skip fighting product market fit and then scale up 10x easier. So, the idea here is what you're trying to identify is what “Is the core need they have that enables us to exist in the first place?”
And then, when you do that and you identify that core problem in need, how do you articulate that in a way that's going to strike them in their heart or activate a part of their brain to where they don't just say “Yeah. I'll have a conversation with you”, they actually ask to have a conversation with you which I think many people may find that a pretty novel concept that a prospect would actually ask to talk to you. But if you focus on articulating that problem the right way, many of them will say “Hey, can we meet?”
As opposed to when you're obsessed of approaching a product market fit your shoehorning and you're asking yourself “How do we make them buy from us?” and when you're asking how do we make them buy from us, you're fundamentally looking at it the wrong way. So, if you focus on problem market fit, your marketing becomes easier, your sales become easier, even your product development decisions become easier and ultimately the product doesn't sell itself but I would say it does tell itself.
David [13:25]:
Is the core to this early or at some point just customer conversations to understand the product and the problem market fit? Like you're saying, is that just literally going on out there and talking to as many customers as you can? Talking to the market, just aggregating data is that step one to get this whole system going?
Rajiv [13:46]:
The more you can be informed by actual customer conversations or potential conversations, obviously the better. But you can do a lot of this, going off of what you already know about the marketplace combined with intuition combined with like a framework to build. So, like a lot of the companies I've worked with, we aren't poring through records of customer conversations to build their messaging.
We create messaging following the specific like framework and then they go out and use that and then it gets refined based on the customer conversations but I'm not saying doing customer conversations first is bad but a lot of companies just don't have those things documented. So, what do you do if you don't have it documented?
You go off of “Hey, what do we know about this to begin with it allowed us to even build this in the first place and what are some of the things we know we've heard thus far just off of like our own memory?” So, going about this route again, it kind of forces you to be more problem focused and you put your own product on the backburner for a second. And if you do this, you actually force yourself to hold off on promoting your product which in turn forces you to have empathy for your audience.
And I know like any UX people listening will love to hear that word ‘empathy’ and I'll tell you like put empathy up against product features in a cage match and ten times out of ten, empathy will win.
David [15:18]:
How do you create empathy? Obviously, it's knowing their problem but then what is the language in have to conversely say? Like we just have to relate to them on their words or what exactly, how do you derive empathy in your language?
Rajiv [15:34]:
So, the base of it is like keep it very conversational. You ultimately want to get to more and more of what are the exact words and phrases they are using but again, I'll tell you a lot of companies out of the gate have some initial understanding of their market to know if their target audience uses the word let's say ‘patient’ instead of ‘client’ if it's in the healthcare sector, right? Some of those core words already most likely, so from there it is just using that knowledge and building out essentially like your conversational elevator pitch.
And the framework that I always start with is to build out the positioning behind this is something I call ‘The Superhero Strategy’ which I'm happy to go into.
David [16:24]:
Let's talk about it. Yeah. Let's go through it.
Rajiv [16:26]:
So, if you want to be problem centric then this is the framework you want to adopt. The idea here, I call it ‘The Superhero Strategy’ and it is a tool to develop positioning in the marketplace. So, this is step one on the journey. You have to think of your SaaS as a superhero and I like to use Batman as an example because if you look at Bruce Wayne, what was he? He was a dude who fell into a lot of capital and figured out how to leverage technology for public good.
Does that sound like any entrepreneurs you might know? Have a lot of capital and using technology for public good. So, you have to think of yourself as Batman. Now, if you're Batman, David just open question here. Generally, what's going on that Batman decides to come in and save the day?
David [17:16]:
Well, there's typically something wrong happening around like a crime or something terrible, right?
Rajiv [17:30]:
Exactly, yeah. Crime in the streets, the bank is being robbed, Joker's blown up the hospital, all that stuff and that is when Batman decides “Okay. Hey, it's time to save the day. Something wrong is happening”. What I will see a lot of SaaS companies do is try to be Batman on a sunny day. What I mean by that is like right now in Chicago, it's like 85 degrees outside Fahrenheit and people are out like they're cool, right.
So, people got their kids at the park, taking the dog for a walk. If it's a day like today no one has a care in the world and like you're not going to see Batman swoop in and be like “I am here to save you”, right? Because if he did, you know how people would react? They would go “Oh my God. Who are you and why are you wearing that cape and stay the hell away from my children” right? You have the exact opposite impression of Batman that he would want to have.
So, in the same respect, that's what I see a lot of SaaS companies do is they try to save Gotham on a sunny day. So, here's the Superhero Strategy. In order for a superhero to exist, there has to be three things in place first you need to have a damsel or a dude in distress, you need to have a village on fire potentially coupled with a super villain. When you have those, you can then activate a superpower and with these three in the arena, then the super hero can come in and save the day.
So, you've got person in distress, village on fire, super power and super hero or if you drill that down into more business centered language, what that creates is target audience, problem, approach and your solution. When you go through this positioning exercise again, you force yourself to think about the customer before you ever think about your product.
David [19:23]:
I like it. I think it's an exercise that many SaaS entrepreneurs and entrepreneurs in general should go through before they even start to build up right even into that MVP. Making sure there is a problem big enough worthy to solve that there's going to be economic viability in the marketplace for that problem if it produces a big enough problem but I love that. I think that this is a critical piece.
So, once you have that positioning and you're understanding more of the problems in the market then you go and you start working on things maybe to raise money for your elevator pitch deck and you have another formula called ‘The Que Pasa formula’. What does that mean?
Rajiv [20:01]:
So, Que Pasa is the step two. You build the Superhero Strategy first to get your baseline positioning out and in the Superhero Strategy, you're not worried about how it sounds you're really kind of like just like doing bullet points and pretend doing a brain dump. From that, you create Que Pasa which is the formula that I developed when I started this to craft a pretty much perfect elevator pitch, give you a 10 out of 10 elevator pitch every time.
And Que Pasa if you're familiar with Spanish, you would know ‘Que Pasa’ means “What's up?” or “What's happening?” and that's what I always tell “Hey, when you're giving your elevator pitch, all you have to do is tell people ‘what's up with your business?’” Que Pasa; PASA - problem, approach, solution, action. When you craft an elevator pitch in that formula, what you are successfully able to do is create context, frame of reference and a degree of empathy with your target audience before you ever talk about yourself.
So, if anyone listening was to rewind this and go back to the first question you asked me around like “Hey, introduce yourself” and I said “Let me give you my elevator pitch”. What did I tell you? I said “Hey, founders talk to me about how they say they suck at telling their story” and it's impacting their close race, their lead quality and getting everyone on the page internally. I come in to help them not suck, here's what I build for them; right now all that's doing is following the PAS of Que Pasa.
And then your action, PASA is your call to action like what do you want people to do? So, if it was for example website home page copy, action might be ‘click to request a demo’. If you were in conversation with someone, it would probably be weird to say ‘click to request a demo’.
David [21:55]:
You should say it.
Rajiv [21:66]:
But what you'd probably do there for action is ask the other person a question to get them talking but that is that's how you craft a clean elevator pitch and one that is inherently designed to get out in under 60 second. And to me, the elevator pitch is so vitally important, it is arguably the most important thing because it serves as the bedrock for all of your messaging then that you're going to develop in your sales and your marketing.
I like to look at the elevator pitch as the movie trailer and the deeper interaction you have with the prospect is the movie. And how often do you see a movie trailer and you're like “That movie looks terrible” and you're like “I can't wait to see it”. Those two sentences rarely ever add up unless the movie has like the rock in it and you're like “Well, it's got the rocks. I'm going to see it anyways”.
David [22:51]:
So, style with written language or how you talk and I think on your website you said make sense. You're talking about understanding the problem, we're talking about coming up with our positioning with a Superhero Strategy, doing the Que Pasa, elevator pitch, so much of what you talked about also has a unique flair to it. I think you're obviously very good at this. You've dialed in to how to be entertaining, how to add personality and story time which is so much about copywriting, right.
Like finding your own style with written language or how you talk and I think on your website you said make sense. You're talking about understanding the problem, we're talking about coming up with our positioning with a Superhero Strategy, doing the Que Pasa, elevator pitch, so much of what you talked about also has a unique flair to it. I think you're obviously very good at this. You've dialed in to how to be entertaining, how to add personality and story time which is so much about copywriting, right. Before a lot of com before a lot of companies to start thinking less like an entrepreneur, more like an entertainer bringing some edutainment in some level, right? Can you elaborate on that? Like what does it mean to bring in that style, that flair, that uniqueness and how does that actually help things like your elevator pitch or your positioning or your website language?
Rajiv [23:44]:
Yeah. So, it's a little backstory. So much of my own personal influence is not just on the sales marketing branding side of things but it's also rooted in entertainment. Since high school, on the side, I have been a hip hop artist so words mean a lot to me. I guess is what I'm trying to say there but specifically looking at like for several years when I watch different pieces of entertainment or listen to entertainment, I look at it through the lens of what can we learn and apply to the business world?
And I think so much business communication is so stuffy, it is so rigid, it is so technical that it scares people away. So, if we borrow from the entertainment world, we can make business communication way sexier and interesting. So, really thinking about okay if we are thinking less like an entrepreneur and more like an entertainer, what does that mean?
I mentioned before we're trying to generate empathy with potential customers and entrepreneurs as I just said, tend to be so product minded and just so in the weeds of their own company that their empathy muscle has been severely weakened. So, the mindset to adopt to help overcome this is think like an entertainer because an entertainer’s goal is to form an emotional connection with their audience. Get them to feel a certain way. So, like David, who's your favorite and/or music artist?
David [25:12]:
Oh man. That's a tough one. Coming up top of my head, Keigo right now.
Rajiv [25:18]:
Okay. Is that a DJ?
David [25:20]:
Yes, probably more like a DJ.
Rajiv [25:22]:
Okay. So, let's say Keigo goes on stage at like Madison Square Garden and although he's DJing, he's probably going to say a few words to the audience to start off and he's going to be like “All right. How's everybody doing?” It's a ‘he’ yeah?
David [25:35]:
It's a ‘he’. Okay.
Rajiv [25:37]:
He's like “Alright everybody. How are we doing tonight?” and everyone's like “Yeah. We're doing good” and then, Keigo is like “All right. So tonight, what I've got for you is every song I have ever recorded but also every song I have ever had in my backup files that I didn't actually release and I've also got every version of those songs and every iteration of it and we're going to be here for the next 48 hours because these songs are really important to me even though you don't care about them. Who's with me?”
David [26:04]:
Make sense.
Rajiv [26:05]:
What Keigo is going to do is play a specific set list because Keigo's goal is to get you to leave Madison Square Garden feeling a specific way and Keigo knows that means having to cut out songs that might be important to him but he knows are not fulfilling the larger feeling and story he is trying to unfold that night. So, in the same respect, you have to as an entrepreneur, as a SaaS marketer, as a SaaS salesperson, you have to know what your set list is and stick to that set list.
And yes, there might be like a little jam session in the middle of the set but that's because it makes sense based on how the audience is reacting at that point. You're not going in with everything in your catalogue. You're going in with a specific set list. That's the main way I would say entertainment should be brought into the business world. The other thing I would mention too and actually harder to just further that analogy, you'll also notice actors will cut lines out of a script if they realize it doesn't serve the scene which is serving the larger story.
But the other aspect, I would say that we should look to entertainment is if you think of most of, if not all, but I'd say most of the just like great songs over time from Notorious B.I.G to Bob Dylan and everyone in between. And these are the songs that have lyrics behind them so I don't know if Keigo would really apply.
David [27:36]:
He's got some.
Rajiv [27:37]:
Okay. All right. So, the songs that are like the socially conscious songs. The songs are never actually providing solutions for people, they are actually just illustrating and highlighting problems that exist like he talked about the problems growing up in Brooklyn, Tupac talked about poverty rate all that stuff, right. Bob Dylan, story of a hurricane. He's just it's just eight minutes of explaining what went wrong and what happened as a result.
They don't come into that song and tell you “Here's what I'm going to do about this problem. You think you can't, I'm going to solve them. Here's plan A, here's plan B. Next up, I'm going to show you what I see”, right. That's not how they're doing their songs. They talk at length about the issues that they observe in society or that are happening in their community and it magnetizes audiences because other people feel like they can relate to that struggle.
And that's why thinking like an entertainer and less like an entrepreneur is so important because it also keeps you in that “Hey, how do I connect with my audience based on the problems that exist not based on the product that I have?”
David [28:50]:
I have such a big light bulb moment going off. You're doing such a great job of articulating the points you're trying to get by just using these different analogies and I think that's really powerful and maybe an example of your storytelling and messaging that you're doing so well. I guess my one question and probably the thing that most people are thinking when they hear this stuff is in B2B, going the route of entertainment may be a scary or risky thing.
Is there a line that you have to worry about between being professional and having some image of like “Hey, we're a B2B company, we work for you and we're a young startup and we're going to use more apathetic language and more entertainment driven storytelling and stuff like that”. Is there any fine line that you have to worry about that can actually then negatively like affect your image or your position?
Rajiv [29:42]:
Yeah. I'm glad you asked that. What I want to communicate here is the lessons learned is what we're applying to business. I don't expect Demio to go to your top prospects door and let's just start playing like a live concert at their doorstep. I don't expect companies to get cookie or kitschy or like cute with their messaging unless that's on brand for them. What we're doing here is taking that notion of caring about the audience and being in service to the larger story at hand. That's what we're taking from the entertainment world.
You take that mindset but then, you match it with “Okay, what do we know about our audience? What are they going to react to? If we're selling into enterprise, let's make sure we are presenting ourselves in a way that enterprise would buy from”. So, I'm not saying like take this information and just like basically act like a kid with it. It's take it, use the mindset and create thoughtful messaging for your particular audience.
David [30:52]:
That's it. Makes sense. So, once you have this messaging really fine-tuned, you've really taken the time to not only do the research but understand what your elevator pitch is, what your positioning is, you have lessons learned from being an entertainer all that dialed in, there's three or four areas that you can take that messaging, right.
Into marketing, into sales, internally into the company, into your sales demos itself, so let's talk about a couple of those. And I think one question that I asked specifically at however who is doing a very big messaging revamp on one of the podcast episodes we had recently, talked about the pains of distributing it into the team. How do you recommend distributing that messaging into the team so that it becomes an organic part of that company fabric that company DNA?
Rajiv [31:38]:
I think the worst thing that could happen is you put a lot of resources and time and energy into developing all this only to just like send it out to the team as an email attachment and then they never look at it. So, step one is making sure that while you're still in like message building - message development mode, you're not hiding from the team that you're doing this work but you want them to know and you'll want to pull in specific team members at certain times to get input or feedback.
Especially if you've got a team of SDRs and BDRs like they're on the front line so you definitely want their input up front over “Hey, what are the things you're hearing from the marketplace?” That way when you are ready to distribute, those individuals feel they have some inherent stake in the game and will be much more likely to champion it throughout the company. Once you've finished building out the messaging like in my process we build out that playbook, you want to build some hype around it.
What I've done with the SaaS is I've worked with is a whole day rollout meeting. So, like a training day, if you will. And this will look different for a team of four versus a team of twenty and a meeting, it can be anything from like a zoom call all the way to like a full day event depending on the size of your company. And during that training day, we're not just saying “Hey, here's our messaging. Start using it”.
We're explaining the philosophy behind of it, we're showing the breakdown of the frameworks, it was built from “Hey, why are we choosing to say this and not that? How does it get tweaked based on the job discipline or the scenario?” and then this training day is designed to deliver the skills and the knowledge.
The key is that skill and knowledge are both perishable so you can't let it end there and whether a company does this on their own or like what I've done is I will meet with those team members roughly once a week for about a month, to see how they are adopting it, where are you having trouble? What insight have you gained from your conversations to improve on this and make it even better? And so on and so forth from there.
So, you want to have a very thoughtful rollout process so you don't waste all the effort you put into developing the stuff.
David [33:45]:
I think so much of getting the context of a new procedure or a lesson or messaging is so critically important to you because then it also helps you understand why those things have changed I think that was a very astute point that you made. I love the idea of that continued education over kind of like the next few weeks or months just to continue to refine that and make sure everyone's on the same page.
Rajiv [34:08]:
Yeah, sorry. You'll see too, like especially with the younger generation coming into the workforce, like Millennials through to whatever's behind Millennials which is I think Gen Z. And I'm a millennial, I’m millennial by age, I sort of feel like I'm more of like sometimes I get the jokes of like “Old man Raj” but well you'll see what a lot of Millennials in the Gen Z is they will not tolerate “Hey, boss said this. So, you have to do it”.
They have to know the rationale and the why behind it to get on board with it and if you don't give them that they will rebel.
David [34:42]:
Yeah, purpose. The purpose of why they're doing it. That makes sense. So, moving that into, we talk a little bit about like the sales team in SDR, SPDRs but if we're going to move that into marketing and we're going to build some outbound marketing emails which I mean your elevator pitch is critically essential in that. You have like 10 seconds to get someone's attention in an email if they even open it.
So, how do you recommend bringing that company messaging into those outbound campaigns and how can you build this out to get kind of the maximum effect from those emails?
Rajiv [35:15]:
Yeah. So, I would say most SaaS is doing outbound so that could be cold emails, cold calls, LinkedIn outreach etcetera. A lot of them are in that product first mode so I think a fun way to do this would be like; let you and I create a SaaS on the fly and I'll just like throw a hypothetical sample outbound message at you. So, like let's say we're selling into midsize accounts companies around like 200 - 500 employees, David make up software that we're selling.
David [35:43]:
A software that gives you analytics for your HR team.
Rajiv [35:48]:
Okay, yeah. HR analytic is perfect and who are we selling it to? The CEO or the HR?
David [35:54]:
The director of HR probably.
Rajiv [35:47]:
Okay. So, we got director of HR and we're selling analytics for your team more or less. What about the name to be?
David [36:04]:
HRLetix. God, I'm terrible with names. You are the name guy.
Rajiv [36:09]:
Okay. HRLetix. Let's say because that sounds like, I hope that’s not an actual company.
David [35:14]:
That's not an actual company.
Rajiv [36:16]:
Okay. So, HR, we got a midsize or a company selling into midsize accounts, selling it to HR directors, selling data software, data analytics for HR directors and we're selling into that director themselves, So, here's what a sample cold email from this company is probably going to sound like and I'm sure as you hear this, you'll be like “Yes, I've gotten thousands of those in my inbox”.
“Hi, David. Hope you're having a nice week. My name is Raj and I work at HR and artificial intelligence analytics provider for HR solutions. Our AI software makes driven decisions a breeze for executives like yourself. This is useful for forecasting, team deployment, future hires and other vital functions. Our customers include companies like active campaign, panda dark and we work slabs division. One customer sprout social was able to use HRLetix.AI to reduce their annual turnover costs by over 50%.
What's the best way to get twenty minutes on your calendar? Here's my calendar link. Thanks Raj”
David [37:46]:
I'm pretty sure I've read that email before.
Rajiv [37:47]:
So, right. So, like that's how most companies are doing their outbound and yeah, it's very product focus. Like all that email is saying is me, me, me, right? So, what you want to do is use that K plus a template and infuse it into the outbound message.
So, I'm just going to take a stab at what the solution here would be or what the problem this person is experiencing would be. So, instead it'd be like “Hi, David. Hope you're having a nice week. I've been speaking with several directors in HR at companies like Active Campaign ad (inaudible) and they've been telling me they've been having a really tough time figuring out how to better forecast their turnover.
And because they can't figure this out, what they're finding is that their turnover costs are really high, their own subordinates don't trust their decision-making and they are running up against low budgets year after year. My name is Raj with HR Letix.AI”.
And then, basically you just say there was like the value prop of like those three points that were negatives before. “In fact, we had one customer sprout social who was able to use and they saw in the first three months, they were able to prevent two or three more employees from actually leaving the company. This was a huge gain for them. Are you interested? Thanks Raj”. And that’s it.
David [39:37]:
I love that. So, much more focus on their pain early on. Like you said that Que Pasa early elevator pitch in the beginning and at the end, they're used to testimonial. Is that part of the X to Y Paradox that you typically work through with use?
Rajiv [39:49]:
Yeah. So, the X to Y paradox is a key component of this for when I mentioned that case study at the end. This is something that I discovered recently and what you'll often find an outbound messaging is companies will show you their best case study, right. Like “Hey, one customer was able to reduce spend by 65%, right”. And you mean well by showing that because you like pumped like “Hey, we had this awesome case study”.
We got to tell everyone about it because when they see these results, they're going to want to buy from us. But the X to Y Paradox essentially what it's saying is that your current customer is in a state of X and when you come in with this amazing case study, I call it your ‘Alpha case study’ where the results were so massive. You're trying to convert them to a state of why and people generally, are stubborn human beings. They'll try to resist change at every possible turn.
So, when you say “Hey, we've got this amazing software and by the way, it's going to help you reduce spend by sixty percent because it happened with these people over here”. They are going to immediately shut you down because when you do that, you're speaking to the rational brain and what the rational brain is going to always do is try to rationalize against change. So, the brain is going to react in pretty much one of two ways.
It's going to say either “Yeah, 65% huh? What numbers did you have to fudge to make that look attractive?” Or the brain is going to say “Yeah, they may have gotten 65% but our situation is different so that probably wouldn't work for us”. They'll find some way to say “Hey, that's not for me” and that is the X to Y Paradox. You think what you think by showing your alpha case study of massive customer success. You are going to attract more people interested but the reality is it backfires.
So, what you want to do instead is what I call the X+1 effect and the X+1 effect has two components to it. Component one is to make sure you are generating empathy upfront in your outbound messaging. So, identify that problem first and what I'll also say David, is notice how when I gave you like the sample mock-up email of like the good way to do it, is I displaced the problem across the marketplace. I didn't send you an email saying “Hey, David. I know you have this problem”.
Because if I did that, you'd say “You don't know me. Get the hell away from me.” Instead, I just placed it across the market. I never directly accused you of having a problem all I said was “Hey, I've been talking to a few other people who are very similar to you. And these kinds of companies or just generally in the marketplace and they are telling me these are the issues they're facing”. So, I'm able to highlight the problem without directly ever saying “Hey, I know you have this problem”.
Because then, what you can do is basically identify yourself within that little story and you then, also see me as a person you can trust because I'm having conversations with other people in the industry. I'm not an outsider trying to tap his way up, trying to tap the glass trying to get in. I'm already in the game. I'm in that arena with them so there's more trust developed. So, part one of the X+ effect is generate that empathy with the problem but displace the problem across the marketplace.
And then part two of the X+ effect is when you throw down your case study, throw down what I call an “Omega K study’. Omega is the last letter in the Greek alphabet so basically, if they are in a state of X show them your Omega K study which is an example of a customer using your product who is at a state of X+1. Meaning they have gotten some incremental gain using your product. It's not massive success, it's just incremental gain because now, the believability increases.
Now, you're saying let's say it's like sales intelligence software, what you're doing is saying “Hey, so and so used our product and was able to close two more deals per month over the first three months”. Now, it's something that's believable because all a sales director would want to do in that case like they're looking at their team's pipeline, I know and what they're saying to themselves is “If Lindsey could just close two more deals this month, she'd be in really good shape”.
All right. So, you're making it believable and what you also want to do is have some type of qualitative effect to that case study so not just the hard numbers but so-and-so said it helped them in this way and this was the result they experienced.
David [44:40]:
This is brilliant stuff. I think all through this whole call, I've learned a lot and I'm really thinking in my head how we can change some of the campaign's that we have, how we can update our own messaging and I love the way you phrase the stuff it's just it's so well done. So, Bravo there.
Rajiv [44:56]:
Thank you.
David [44:57]:
Now, I want to kind of move forward and look forward in 2019. There's so much changing in the SaaS marketplace. It's getting more competitive, different people are going more upmarket. We're going to be the new challenges and opportunities that you see in SaaS specifically around marketing and messaging you see coming out this year.
Rajiv [45:19]:
Well, yeah. It does. I guess I see one opportunity and two challenges and one of them has nothing to do with marketing and messaging. But opportunity; over the last five to ten years, there has been an emergence of the field known as sales enablement. And there's even like sales enablement conferences now, right?
David [45:50]:
Yeah. I actually just got off the Showpad on the last show and their sales enablement and they're talking about that the whole industry's blowing up.
Rajiv [45:57]:
That's awesome. And Showpad is a company I really admire all right. And they've built the conference around sales enablement. So, the thing with sales enablement is companies will hire a director of enablement somewhere around like the hundred employee mark. And they'll hire them for like 100 to 120k salary per year.
Often times, this is actually too late because the messaging is so frayed by that point that with each sales and each sales and marketing team member that gets added, it gets frayed more and more. And then, all these people who are already on who are already hired who have been there, have developed their own habits that they don't really want to break. So, instead of spending their time building sound proactive material, the enablement director is basically spending their time building reactive habit breaking material.
So, I think what we are going to see or that we need to see more of, is companies getting on this enablement at an earlier stage. Whether that's through hiring it out as like a fractional role or just making their early VP of sales or marketing take on more of this responsibility so they're not just like focused on like pipeline management, they're also looking at “How do we develop our team here?”
That's the opportunity I see and I don't know if it's so much like “Hey, I think the industry is going there” as much as I see it as like “The industry needs to go there”. The two challenges then, I would say are I think as more SaaSes are looking to raise funding, investors are going to get more and more picky about the type of SaaS they will invest in. And they will be very like discriminatory towards the ones that create network effects because they'll see those as the most attractive.
So, if someone's not familiar with that, what I mean is like in order to use your product, someone else has to use it as well. For example like I use Calendly the scheduling software but Calendly only works if someone else uses my link and books a meeting. And then, so just by one person owning it or purchasing it, two people are now users of it and now, that second person is more likely to look into it and want to buy it. So, that's like network affected a small scale and they ballooned.
But I think the point here is that the network effect for products have CPA reducing over time built into their business model which is ultimate like the most attractive thing for a business actually for an investor. And then, the other challenge i would say which has nothing to do with marketing or sales or messaging is just I think we need more diverse faces in SaaS.
For the most part, it's a lot of heterosexual white males at the helm and I think we need more women voice and the thing is you'll see like women get like head of marketing roles but they're not so much the CEOs. So, I think we need more women CEOs, we need more people of color CEOs and more people from the LGBTQ community out there.
David [48:58]:
I love that. Now, that's really well said and I completely agree. I think that's something that we're going to have to shift you as our marketplace evolves and that's the next evolution. So, all great answers and what I want to do now is I want to jump over to our lightning around questions. Just five quick questions for you. You can answer with the first best thought that comes to mind. Ready to get started?
Rajiv [49:19]:
Let's do it.
David [49:20]:
All right. Let's do this thing. What advice would you give for early stage SaaS companies starting marketing today?
Rajiv [49:27]:
It might be a little bit of a repeat of what I said before but really story is what sells. So, like if you're starting, don't just invest your time into product development. I would almost argue for every hour spent on product day, spend fifteen to thirty minutes on developing the story.
David [49:47]:
I love that. What skill do you think is vital for the marketing teams to improve and build on today?
Rajiv [49:55]:
Listening. I would argue listening as a skill.
David [50:00]:
It's probably driver to empathy, right?
Rajiv [50:02]:
Yeah, definitely. I think sales needs to do a better job on calls of listening to the customer instead of just getting into that mode of like “I already know what they're going to say and I'm basically not paying attention so I can wait till it's my turn to talk” but I knew better job on calls of listening but then also, relaying what they heard back to the marketing teams so that they can push out better content.
And the marketing team needs to listen to what sales is telling them not just assuming they know what's best for them. And I made up creating materials that the sales team ends up not using.
David [50:36]:
Such an easy solution to a big problem that can give massive results so I love that. What about a best educational resource you'd recommend for learning about marketing you’ve got?
Rajiv [50:44]:
I mean I don't mean to suck up but I think the SaaS breakthrough podcast is a pretty good resource. I do mean that like I've probably listened to a dozen episodes and nearly every time, I'm like “Damn it. Why am I in my car while I'm listening to this? I wanted to write that one”. So, a lot of times, I have to like go back and like listen like a five minute clip from an episode so I can jot it down.
I would also say to how I built this podcast if you're familiar with that, I think that's really good for not just the marketing growth aspect but like that the overcoming the struggles that I think every founder can relate to and just seeing like what other crap did other people have to eat to get to where they are to help you just kind of know that like “Hey, it might be tough but it is doable”.
David [51:34]:
Sometimes, it's easy to get stuck in our own story talking about story. We forget that other people go through the same challenges and it is okay. What about a favorite tool you can't live without?
Rajiv [51:44]:
I think every day, I'm using Calendly and Zoom. Those I definitely can't live without those and also MailTrack. I will say though a new tool I just started using that I really like is It's free and basically, you can create a landing page in like 30 seconds.
So, like the X to Y paradox e-book that I created, I used to create the landing page and the templates that you pull from are so simple and so clean and neat and they were designed in mind to optimize conversions. My download rate on that e-book right now is at 51%.
David [52:30]:
Rajiv [52:31]:
I think I've done fifty one percent, I mean except for like grades in school which I did way better than that, I don't think since then, I’ve ever done anything at a fifty one percent clip. So, I would highly recommend using again. It's free and it's you can put together a really attractive landing page for say a lead magnet in 30 seconds.
David [52:48]:
I'm going to get on that, check that out after this podcast. That sounds amazing. And we'll wrap it up with a brand business or a team that you admire today.
Rajiv [52:58]:
In the SaaS world or just like the tech world, I would say Gong.IO. I absolutely love every piece of content they create and they're so on point with the advice they dole out. In general, I have to go with what I've been saying since I was 8 years old and that's the WWE.
David [53:19]:
You're the second person on his podcast to say that.
Rajiv [53:21]:
No way.
David [53:23]:
Yeah. Someone else has said that WWE and their storytelling techniques are so good. So, that's fantastic. So, there you go guys WWE one of the best storytelling areas to go. But I want to say thank you so much for joining me today. We went through a lot, this was a longer podcast that we talked about a ton. Where can people find you and find out more about your different strategies and formulas and all the stuff we talked about today?
Rajiv [53:46]:
Yeah, for sure. So, I'm found very easily at I also have a podcast called Startup Hypeman, the podcast where we talked with many different founders and startup leaders on how they're growing their companies. If you want that X to Y Paradox, that e-book, and get at me on LinkedIn too. I think I post most frequently content on LinkedIn so just search Rajeev Nathan there and you'll find it connected me personally.
David [54:16]:
I love it. Well, thank you so much for joining me. Have a great rest of your day and I appreciate all your time.
Rajiv [54:21]:
It was my pleasure, thank you.
David [54:23]:
All right. We'll talk to you soon.
So, how amazing was that episode? Raj really is the heavyweight champ of storytelling. He had a great job of articulating and really bringing his concepts to light. Things that I think created new light-bulb moments for me and how we're going to now approach our own messaging. So, definitely recommend you go back and listen to different segments of this episode so many golden nuggets and tips all throughout.

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