
Grow Your Software Development Agency With ManagedCoder · 2023-04-13 · 19 min
Key moments - from our scoring
Substance score
44 / 100
Five dimensions, 20 points each
Ryan brings deep sales expertise from scaling a business unit to $30M ARR to this conversation about the core challenge most agencies face: insufficient pipeline. The episode digs into two critical problems: most companies rely on outdated ICPs rather than analyzing their actual best customers (biggest deals, fastest closes, biggest losses) to identify patterns. His Five-by-Five Method helps agencies discover that typically 70-80% of revenue comes from 2-3 verticals, enabling them to niche down and command premium pricing. The second half tackles outreach strategy in an era of email saturation. Rather than using ChatGPT to scale generic outreach (which just adds noise), Ryan recommends the opposite: sending 15-20 deeply customized emails using ChatGPT strategically for research - identifying target KPIs, challenges, and solution messaging. He also advocates old-school differentiation through phone calls, direct mail, and building a podcast to interview ideal prospects. For service agencies specifically, Ryan emphasizes quantifying outcomes: reframe the $5K website cost as an investment by showing past clients' sales increases. In a down market, he advises narrowing focus on thriving verticals (AI, cybersecurity, early-stage venture) and pulling the quality lever rather than volume.
Analyze your five largest closed deals, five fastest closes, and five biggest losses to find patterns in verticals, titles, and customer profiles. This typically reveals 2-3 verticals driving 70-80% of revenue, allowing you to niche down, charge premium prices, and close deals faster.
Send 15-20 highly customized emails instead of 100+ generic ones, using ChatGPT to research prospect KPIs and challenges. Supplement email with alternative channels like LinkedIn direct messages and video, and consider old-school tactics like phone calls or direct mail to cut through noise.
Always lead with tangible outcomes, not just price - e.g., "My last five clients saw a 40% increase in sales from website improvements" backed by testimonials. This reframes the service from an expense into a measurable investment.
Don't stop outreach; instead, narrow focus to thriving verticals like AI, cybersecurity, and early-stage venture companies (seed/Series A), and rely more on referrals from existing customers rather than expanding volume.
No - because everyone can use it, generic ChatGPT-generated emails just amplify noise. The advantage comes from using ChatGPT for research (KPIs, challenges, messaging) to inform truly customized outreach, not scaling generic templates.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode offers a handful of actionable tactics - the five-by-five PCP analysis, quality-over-quantity outreach, and podcast-as-pipeline - but much of the runtime is consumed by generic sales truisms (personalize emails, ask for referrals, call people) that any B2B operator will have encountered before. The density of genuinely non-obvious ideas is low for a 19-minute runtime.
everybody is getting because of the beautiful availability of automation and sequences and everything everybody's getting hammered with cold email, cold, nondescript, generic email
send out like 15 to 20 just customized emails based on knowing really deep level of understanding of their business
The 'perfect customer profile' framing layered on top of ICP and the podcast-as-pipeline idea are marginally fresh angles, but most of the episode recycles well-worn sales consulting advice (phone calls beat email, personalize outreach, use ChatGPT prompts). There is no contrarian or first-principles argument that challenges conventional wisdom.
I started interviewing my prospects on a podcast. And then what happened is they started asking me, oh, Ryan, what do you do exactly?
you could turn a podcast into like a pipeline, right? Where you interview only the top people that you would like to work with
Ryan has a legitimate practitioner credential - growing a business unit from zero to $30M ARR in five and a half years without an SDR team or marketing - and runs an active sales consultancy, so he is a real operator rather than a pure thought leader. However, he is clearly now in the 'professional podcast guest and consultant' lane, and his advice stays at a level of generality that undersells what deeper expertise could deliver.
I grew a business unit from zero to 30 million in ARR in five and a half years with really no marketing team or no SDRs
I am the founder and ceo of whale boss
There are a handful of real numbers - $30M ARR, Vista Equity as a $90B fund, a claimed 30% drop in close rates, five-grand website example - but most are either unverifiable personal claims or used only as rhetorical colour rather than grounded evidence. Snowflake and Vista Equity are name-dropped without any operational detail about how they actually applied the framework.
Snowflake leveraged it as well as Vista Equity, which is a $90 billion fund that turns $2 billion companies into $6 billion companies in three years
it doubled our deal size every year for five years, even 100X our largest deal size
The host asks broad, open-ended questions ('what are the three advice you can give') and never challenges, probes, or pushes back on any claim the guest makes. Follow-up questions mostly restate the previous answer or pivot to an entirely new topic, leaving several interesting threads - like the mechanics of the five-by-five method or the actual Vista Equity story - completely unexplored.
what are the three advice you can give it to people who is listening to this podcast
So new customer, new customer mostly.
Computed from the transcript - who did the talking, and the words that came up most.
In this podcast, we will discuss some of the most effective sales pipeline secrets that agencies can use to grow their revenue. Our guest speaker will share his experience and insights on how to create a high-performing sales pipeline by focusing on your ideal customer profile and perfect customer profile. We will also learn about the five by five by five method, which can help you identify key trends in your biggest deals, fastest deals, and biggest losses. Additionally, we will explore how to differentiate yourself from the competition by customizing your outreach efforts and using alternative channels such as LinkedIn. If you're an agency owner or sales professional looking to improve your sales pipeline strategy, then this podcast is not to be missed. Tune in now and discover the secrets to building a successful sales pipeline for your agency!
Transcribed and scored by The B2B Podcast Index.
If you're running a software development agency, it shouldn't be too hard to grow. Welcome to Managed Coder Podcast. Tune in every week to find out how to grow your software development agency and help you to solve your day-to-day problems. With 20 plus years experience running an agency, please welcome your host, Shahed Islam.
hey ryan welcome i spoke with you last week so we talked about few topics and i thought i should welcome you on our podcast um can you introduce yourself yeah so i am the founder and ceo of whale boss i've had well i'm also the host of the scale up show so i interview sas ceos and they deconstruct their best strategies for growing their business and leveraging that. So I'm a podcast host and I'm the CEO of Whale Boss, which is a sales consultancy company where I help tech startups grow their company specifically around pipeline, whether they're having a challenge with enough pipeline and or converting sales specifically for mid-market plus.
So ideally companies that want to grow and multiply their largest and best customers. So I take the principles that I created and kind of found when I grew a business unit from zero to 30 million in ARR in five and a half years with really no marketing team or no SDRs. So that's a real quick background on me. I could go on in different details, but let's start there, man.
You have a lot of experience and that's where I know I've been talking to a lot of agency on our mostly software development agency. There are some people in India and other places. And, you know, one question they have it, they cannot build their pipeline, you know, enough to run their business. And what I have identified that, you know, sometimes they are not niching down and up, but also like the strategy they have it to reach out to people.
So with your experience, if you have to give, you know, talk about a few points, what are the three advice you can give it to people who is listening to this podcast. Yeah, and it's funny because it's like pipeline, no matter what business you are in, it's nine, I don't know, maybe not nine, maybe eight times out of 10, the biggest challenge that companies are facing when it comes to growing revenue. And so there's two core buckets that I would kind of put this in in terms of solving that problem.
And one is basically most companies look at what's called their ICP or their ideal customer profile. That's whether it's the company size, the persona vertical, all those details, right? So the area that I look at that I think really, really helps, and this is especially relevant because of how fast things are changing, like you need to do this at least every six months, is also look at your perfect customer profile. So this is a strategy that I created as a rep.
I did it in a go-to-market and it doubled our deal size every year for five years, even 100X our largest deal size, while also speeding up our sales process. Snowflake leveraged it as well as Vista Equity, which is a $90 billion fund that turns $2 billion companies into $6 billion companies in three years. And so a real quick breakdown on how you could leverage it in your business today is what I call the five by five method, right? Five by five by five.
So what it is really is it's you take and look at the five largest deals that you've closed as an organization. You look at the top five fastest deals you've closed as an organization and the top five biggest losses that you've had. And what you really want to do is look at the demographics, like what verticals they're in, different titles that you've worked with, and really try and find weird outliers on why those big deals close, why they close so fast, and why you lost really big deals too.
And just by doing that alone, what usually happens is we'll come to the top. And this especially works for horizontal solutions, like they can work across any vertical. you'll find that there's typically two or three verticals that have 70 to 80 percent of your revenue. And I see this all the time.
I just saw this the other day. And essentially what happens with that is if you become a niche specialist with that and specifically target those 70 percent, 80 percent type companies and become the expert in that space, you could charge a lot more. Your deals will continue to close faster. And then at the same time, you will lose a lot less business.
So that step number one right Is really defining your perfect customer profile Step number two is everybody is getting because of the beautiful availability of automation and sequences and everything everybody's getting hammered with cold email, cold, nondescript, generic email. So what's happening is the intensification of noise is massively accelerating. It's going through the roof, right? Because there's so many people that could send so many large amount of emails so fast and easy that people are just getting absolutely hammered, right?
So I would advise if you're struggling with that, go in the exact opposite direction. Instead of sending 100 emails out a day or two days over a two-day period over a sequence, send out like 15 to 20 just customized emails based on knowing really deep level of understanding of their business. You can take it off their website. You can take it off their LinkedIn profile.
I would recommend doing that. You could also drop different examples of like voice to text, or I should say not voice text, but voice direct messages on LinkedIn. You can do videos on LinkedIn, direct messages, and use an alternative channel like LinkedIn versus email because they might get maybe five direct messages a day versus 500 emails a day, right? So those are a couple of really quick examples of like how I would target people and how I would kind of approach it.
So, again, I think where I have seen the struggle with a lot of agencies, even I receive a lot of emails that just like you said, customizing it, but not knowing that what problem I'm going through when they're reaching out. So that research part, how do they start if a sales rep or a CEO is listening in? What do they tell their team that start from here? Because a lot of people don't know how to do that research.
A little bit more if you can provide us some information. Yeah, so I would say there's a couple of ways. First of all, if you do step one and you research your own customers that you've had success with, it'll leave really good clues, right? And most people don't even take the time to do that.
They set their ICP once and then they forget it, right? So I would do that. And then the other thing I would do is like, it's really simple. So I wrote a chat GPT post on this on LinkedIn that went viral, but essentially like it's so simple and easy to execute on that.
And here's the exact formula on how to do it or even the prompt, right? Basically jump into chat GPT and ask whoever you're selling to, ask what the five top KPIs that that role is evaluated on, right? So really simple. Even if it's the CEO of a small business, you could ask, hey, what are the top five KPIs that a CEO of a $5 million business in tech is most concerned about in a down economic environment.
And you want to use that word for word, right? So look back, you want to be specific and give it context in terms of that. So what will happen is it'll spit out the typical five key focus areas that a CEO in that space would try and, or I should say, have at that point in time. Then you do another prompt, which is very simple.
It's like, hey, what are the five biggest challenges they have with meeting those needs? Right. So you're taking it from like, OK, what are they focused on and what are their biggest challenges? Then the next step is, okay, if I were to provide agency services for creating, let's say, websites, how would I make my solution - these are prompts - how would I make my solution relevant to someone that's experiencing the five challenges above?
And then, boom, that'll give you a really, really solid foundation that you could work from. And then what you could even do is you could ask it to cut that up into five different emails, addressing each problem individually in each email with your solution and how it helps. That's just one example. Right.
Another example of research that you could do is I think. Like and I know I said, look at your own existing customers, go back to your best customers and like literally sit down or have a quick call with them and just say, hey, what was the exact reason you chose us? Why did you buy us over everybody else? Who else did you look at?
What other solutions did you consider And then this will put you in the mind of the buyer And then what you could do is basically replicate that in your messaging in your outreach in your connection with them and use those exact words and you'll be very very successful if you leverage that formula no this is really really good you know you are giving us the prompt and you know from chat gpt And my next question would be, since JGPD came in, like the first impression was I was talking to my sales rep and other people.
Oh, now our sales email is going to be a lot easier. I can reply the email very quickly, which is good. They are doing it a lot faster. A lot of these proposals are sent very quickly.
Does it really solve the problem? Like now I am seeing a lot of other people are doing it. So we are back to scare one. Just like you said it, like because of the new tools came through in last four or five years with Drip campaign, I receive hundreds of email now.
Same with ChatGPT. Just because you have it does not mean other people cannot use it and they will use it. And eventually we are back to square one again. So what are your advice that when all these AI tools and then other people are not using ChatGPT or these AI tools?
So what are your advice to those people who are using it and those who are not using it? Yeah. So regardless of whether you're using it, I mean, this is going to sound so like old school. But here's what I'd say.
First of all, everybody's not using it. There's a lot of people that are using it internally for their own organization, but they're not leveraging it in that capability. And I know that because I've talked to multiple revenue leaders on that. However, what I would say is there's a couple of things.
Go old school, right? Pick up the damn phone and actually call someone. You know how many times I get calls from people? It's very, very, very rare, right?
So one, you could stick out by doing that and actually calling someone versus just relying on email. The other thing that you could do is there's platforms out there that are very economical now where you could send direct mail. You could send customized gifts. You could do things like that that are very, very simple.
to execute against that they kind of have you stick out from the noise. That's another one. Third one, and I'm a huge, huge, huge proponent of this, is basically, and this kind of happened to me on accident, where I started interviewing my prospects on a podcast. And then what happened is they started asking me, oh, Ryan, what do you do exactly?
How do you help? And then basically, you could turn a podcast into like a pipeline, right? Where you interview only the top people that you would like to work with that fit your ideal customer profile, your perfect customer profile. And then you could essentially convert them into customers by building a relationship, providing value in advance, and then asking thought-provoking questions to them that make them reconsider, oh, maybe I do need help with this service, or maybe I need help with putting up, standing up a website or improving it.
And that's what kind of naturally happens as a byproduct. When you are talking to the B2B sales and you work with mostly SaaS, you know, selling SaaS, mostly software services, and we are selling services. What do you see the difference? Like when we are selling sales as a service, right?
I mean, service as a, like service we are selling to the customer. Do you have any advice for us that, you know, you should do this? For services versus SaaS, is what you're saying? Yes, yes.
So the real critical thing, because like my entire career or not my entire career, but a lot of my career was selling services. So selling managed services. So totally get it. I think like the number one thing you have to do is establish in the in the customer's mind the first point in which you talk to them or communicate with them.
What's the tangible outcome that they're going to get and quantify it. Right. So I think most people don't do that. They do very, very softly.
So, for example, if someone was asking me to spend five grand or 10 grand on my website, my website is something I'm working on right now anyway. So but I know you mentioned that is where a lot of people that you have in your community are. Right. So someone was helping me with my website and, you know, they were like, hey, it'll it'll cost you five grand to do this.
Right. That would be, you know, I'd be like, oh, five grand for a website. Sounds sounds expensive. Right.
However, if that same person came to me and said, hey, it's $5,000 for a website. However, for my last five clients that I've implemented this at, they've actually had an increase of in sales as a result of the changes we made because of X Y Z And here a testimonial to prove it then it becomes a whole different story It becomes an investment not an expense And so that's where people, I think, could probably do a better job because it's everybody, because of what's happened with Amazon and the B2C consumer market of instant gratification, whether it's Netflix, whether it's Amazon, people want results.
They want it fast. If you don't have results, they're going to get pissed. And so that's something that I would just kind of want to call out, if that makes sense. My last question to you would be like recession, even though it's not officially here, but we see a lot of kind of the market is not stable enough.
And especially for service industry, a lot of people are losing contract right now. What I have seen that a lot of people stop doing sales. They're like, why should I reach out to them, people are annoyed. But my suggestion to a lot of them is that you still have to do your job.
It's almost like going to a gym. You have to continuously go. So what is your suggestion about this recession and what is going on right now around you and what do you see and what is your suggestion to agency owner, whether they should reach out to their customer or not? Yeah.
Are you talking existing customers or net new? So new customer, new customer mostly. Yeah, I think, well, and the one thing I forgot about pipeline, and this is relevant to your question right now, is to ask your best customers for referrals. Really, really do that and focus and narrow on that.
So what I would say is people, I mean, it's not like we've gone through an apocalypse and there's no more businesses anymore. There's still companies spending money. They're just looking at everything tighter, right? However, there are still thriving industries.
So you could look at different verticals or sub niches that are really, really growing now that are growing fast because there are those that are doing it. Like even though venture capital has dried up a lot, let's say versus 21, there's still companies that are getting a lot of venture capital in like the earlier stage round. Let's say seed or series A where series B, C and D might be getting a lot less funding. Right.
so also like cyber security ai companies like those companies really really they need to move fast right so there's there's different areas where uh companies or sub niches or verticals are still growing really really fast you just got to take a step back re-identify those and then go after them hardcore and put all your might towards them so that'll kind of offset the other thing i would say too is this like you know and if you kind of look at it maybe you know your close rates And I looked at this close rates dropped, I think, 30 percent last year as a whole for B2B companies.
And so all you have to do is look at, OK, either what are the levers I can pull? I can pull the quantity lever or I can pull the quality lever of what I just mentioned. And the quality lever is something that I would pull versus just the more button, because that's when you get in a spam bill and you're sending tons of emails and you're not getting the results you want. So no, thank you.
Thank you, Ryan. What is the best way to reach out to you? And what other consulting services do you provide to anybody who's listening in? Yeah.
So there's two core elements, like I said, on how I help companies. And I'm looking at expanding that. But right now, it's either on the pipeline creation, like companies that have a pipeline problem. I have a solution where I help companies ramp up referral-led growth through their existing customers if they have a base or through podcasts as a pipeline.
I also have like a sales conversion revenue sprint that I do with folks as well. So that's what I do. Where you can find me is my website is ryansdaily.io.
I have lots of content on there. My podcast is called The Scale-Up Show. And if you heard me here, feel free to send me an email. It's ryan at whalesellingsystem.
com. And just mention that you heard me on the show. and let me know if you have any questions or if there's anything I can help you with. Thank you, Ryan.
Thank you. I really appreciate it. Talk to you. All right, excellent.
Thanks for having me on. Thank you. Thanks for listening. If you enjoyed this episode and you'd like to help support the podcast, please share it with others.
Post about it on social media or leave a rating and review. To catch all the latest from us, you can follow us on Twitter at Managed Coder or visit our website at managedcoder.com. Thanks again, and we'll see you next time.
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