Watch Ryan Staley of Whale Boss exclusively on Founderpath. In “How I Operationalize AI in 60 Days: 5 Strategic Moves for SaaS Leaders to Double Sales…
Featuring Ryan Staley · Published September 6, 2024
The talk proposes a focused, staged approach to operationalizing AI in a SaaS organization. It connects AI work to a specific retention or growth metric, then covers implementation, team adoption, shared practices, and RevOps use cases.
Find the ideas you need and go straight to the source.
Focus AI on a single metric
“really focus on churn let's go into customer retention and then as you see all the way to the right it could be on customer turn rate Revenue turn rate or product usage frequency and you could build AI workflows to support that specific area to really move the needle the biggest thing I want to encourage here though is because you could do everything with AI what I'm finding is people will do nothing with AI so this focus is the most critical tip of the spear when you're attacking this all right the other step and this how many metrics people do we have in here how”
“looking at a team of 40 okay that's pretty impactful when you look at it right okay so now I'm going to move on to section two I'm going to talk about the Implement train and transition or transform I should say because this is really critical so now that we have the focus the next thing that we're going to do is really look at how it's different and is set expect ations and this is one of the areas where I see it wrong um how many people think that how should I say this uh let's just put consumer I'll was just say consumers generally speaking have a um High”
“that are using it and 90% of the team that aren't and you have somebody who's amazing at doing these things and creating Innovations but they're not being leveraged across the team okay so you want to have it in a centralized repository the next is iterative prompting does anybody know what I mean by iterative prompting at all it's literally one of my favorit okay so we got some AI savy folks in the front row Kyle knows it too he's he's he's raising his hand over there so all it is and this is one of the super coolest functions within chat gbt you have an output you highlight it there's a little”
“staff revops person in here nobody okay Rev Ops Revenue operations okay usually for bigger companies if you have the teams package in chat gbt you could effectively mimic a full-time revops person and basically these were some of the insights that we created where basically able to close rates by 40% improve it increase deal size from 21k to 91k in the situation and attack the Enterprise segment we all did this by”
why don't we just begin right away so one of the things I'm going to do today is I want to start off with a question um so how many people right now in this room have a design AI strategy for their product raise your hand nobody kind of okay so so you could say yes if if you're integrated if it's in the road maybe a better way to asking how many have that in their road map as part of their product right okay so how many people have or how many I should
say people in this room have the same thing for their human capital for their people do they have a road mapap for integrating AI into their team anyone okay so I see one person notd in their head he didn't raise his hand but I give him credit he's not in his head okay so that's what we're going to cover today really because if you think about it we're only hitting half the formula if we're hitting product and systems and internalization right so we're going to talk about how to integrate activate and innovate really how to first start off
and get the ROI out of AI right metrics over mistakes scales with hiring um we're going to implement training transform and then collaborate celebrate and Elevate so we're going to hit on all those areas and after this 20 minutes you're going to truly understand how you can start actuating this with your team the day you get home okay so what I want to start off with is this is like real quick about me in terms of a background um I help companies deploy and implement this so this isn't some Theory I came up with this is from actually working with
go to market teams specific in sales for marketing and executive teams on how to integrate AI into what they're doing from a day-to-day to multiply the output and scale their team without hiring okay um in terms of my results I I spoke on this last year I helped a company go from zero to 30 million in AR with only four sales reps in five years without any kind of funding Str Str or really marketing so I to get highly creative because we didn't have a lot of capital to deploy or we didn't have any Capital to deploy and I always had really
extreme demands and so what I saw from that when I combined it with AI when I got introduced to it about 19 months ago uh from one of the guests of my podcast is that that was a vehicle to really leverage it and stack on top of what I did to grow from that zero to 30 so I'm going to talk about that today and then there's a bunch of other stuff you could read it I don't need to get into it so here's some of the company implementations I've done I've done it for as little as a million all the way up to 30 million on here I'm doing it right now for a $300 million company as
well I don't want to break the scale but the beautiful thing about it is depending on what size you're at this is going to work for anybody whether or not you have one sales rep or your founder Le all the way to having a team of 20 30 50 100 people okay so we're really going to magnify what you're doing from that and so what I'm going to do is break down the different ways where you can quantify the ROI and so I'm going to give you a couple different tools that you can leverage when you get home on how to do that so step one in terms of you can look at through this this is like the eyes and Hower Matrix right a
real simple prioritization category where you can look at outcome or you could look at time right and this time aspect is going to get magnified by the number of people that you have as well as the quantity of repetitions or projects that that team is doing okay if we're looking at the outcome this could be for example we need to increase customer acquisition by 40% over the next 12 months and you could tie it to that so ideally you want to intersect it and have it up to the right as much as possible so that's in terms of prioritization the other way you can go
is kpis okay this is a lot you might want to take a picture of it I had to refine this because I'm like ah they're not going to be will see anything with this this visual right um so basically these are typical cro kpis or Revenue kpis ranging all the way from revenue growth customer acquisition retention sales performance and expansion and upsell so what you could also do is if you're not quite sure on that Eisenhower Matrix that I just showed you you could also look at these areas and say okay you know I need to
really focus on churn let's go into customer retention and then as you see all the way to the right it could be on customer turn rate Revenue turn rate or product usage frequency and you could build AI workflows to support that specific area to really move the needle the biggest thing I want to encourage here though is because you could do everything with AI what I'm finding is people will do nothing with AI so this focus is the most critical tip of the spear when you're attacking this all right the other step and this how many metrics people do we have in here how
many people like metrics in here yeah okay good okay so we got a good mix so this is a very simple way if you want to look at your sales conversions let's say your team isn't doing very good in certain areas you could take this and all this is is like looking at different snapshots of the sales process and what you could see is if you apply different workflow or use cases to different areas as you could see the one at the top in the yellow is the existing the new metrics is the line below it and the Improvement percentage is just for that
stage so if we make an improvement on the amount of opportunities by 10% we make an improvement on the demo conversion rate by 10% and the PC proposal phase by 5% proposal negotiation by 3% and we have a little bit of an uptick on our ACB all the way to the right from 30k to 36k just by stacking those small improvements you're going to have 157% growth okay so that's how simple it is and that's how you start to narrow the focus on where you're
at next thing that you need to do is or this is another option and basically this is what it's all rolling up to this is taken from Salesforce I think there was over [redacted phone] sales reps that this was taken from roughly 72% of time is spent on non-selling activities if you look at the jobs to be done that a sales rep have they have about 24 or 26 different jobs to be done with what they're doing all of them have how actually how many people here are really familiar with the disc profile Pro process anybody know that dis profile
right okay it's a personality um if you look at that it hits on every aspect of the dis profile which they need to be proficient at so the goal of this and what we're trying to do is basically do two things one through AI enablement reduce 30 to 40% of non-selling activities and then move that over to the selling time so how can we double the amount of selling time they have but then also double the level of thinking that they have and the reason and where this story comes from and this is what literally scared the out of me and I'm sorry for using this language but it
scared me to my core do you remember how many people remember when chaty BT came out and everybody's like I want to see if it could replace me does everybody remember that they're like oh I'm going to put it in what my job is right so I'm like all right I'm going to take I had 10,000 hours in Enterprise sales my team so I'm like I'm going to ask it some questions around the kpis of a CIO how they're evaluated their motion spheres and he got like 90% of the way there in three questions all right so I'm like okay if it could do that for me and it reflects I knew that was a good answer
imagine we could do this was GPT 3.5 so we have four o it's out now and if if you you're not keeping up with the large language model race that's happening allegedly strawberry is supposed to come out and allegedly it's supposed to hunx the quality of output that GPT 40 has so stop and let that sink in real quick 100x right let's say it's 10x that's still pretty freaking good right I mean that's what I would say um another thing if we're looking at Roi how many saw the uh article about
Andy jossi at Amazon with what Amazon's doing did you guys see what this just got released last week no nobody saw okay so basically they integrated AI into their developers and this isn't go to market but he said basically it saved them 4600 years of developer time right now that's a big team right 4600 years and 240 million now even if you have a small fraction of that and you can apply it to your Revenue
generating team imagine what that's going to do to your results okay so that's what we're focused on so if we're talking about scaling a team I'm going to break it down to the micro so you can see this even if you save your team 48 minutes a day you have a team of 10 that's going to give you one new basically capacity level capacity you team of 40 that's four new teammates if you're doing really solid at implementing this what's going to happen is those 96 Minutes are going to convert either to two new teammates if a team of 10 or eight new teammates if you're
looking at a team of 40 okay that's pretty impactful when you look at it right okay so now I'm going to move on to section two I'm going to talk about the Implement train and transition or transform I should say because this is really critical so now that we have the focus the next thing that we're going to do is really look at how it's different and is set expect ations and this is one of the areas where I see it wrong um how many people think that how should I say this uh let's just put consumer I'll was just say consumers generally speaking have a um High
expectation that everything goes perfect right away and uh there's no friction whatsoever how many people think that happens all the time right so people expect that out of large language models and it's just simply not the case it's like an alien and then if you look at a SAS solution SAS has a consistent performance all the time this is like a jagged edge so you got to set the expectations with your people that this is going to happen so they don't use it once and then write it off it's like my my daughter she had a bad piece of food and then she writes off that food and never has it again and I have to work on her for four to five years so she tries
that vegetable again or whatnot same kind of concept so this is where it's going with go to market specifically with sales and this is taken from Gartner so right now we're in phase one and two and I'm also an ambassador for the the Gartner community on the sales side we're in phase one and two so this is like more on the reactive side where we're leveraging simple automation or assisted selling what's going to start to happen is we're going to shift from that and how many people have heard of agents in here yeah lot yeah okay so we're moving more to the agentic
structure and I'm starting to see elements of that does anybody use perplexity in here consistently at all or no no if you okay this will be a test perplexity is free you get five Pro searches for free right try perplexity Ai and do a search and click on that Pro feature before you do it you'll see it go through a multi-step process process and it'll visually show you that's what's going to start happening with everything and so this is really going to take off and that's where we get to the autonomous selling um Ilia suev who
was one of the founders and I probably butchered his last name one of the founders of open AI basically identified that he says right now the next phase we're going to that reasoning upgrade which is where project q and and uh project strawberry is coming out for openai with the next model which would be gp5 and then what's happening is agents are the next level to be mastered okay once that happens one of the things he predicted in 10 years there's going to be companies 10 times as strong as Apple because they will have autonomous highs of Agents
working without humans just humans directing some of them okay so this is where it's going here's some actual use cases from sales if we're breaking this down of like how you can implement it in your go to market okay so you might want to take a picture of this but this is everything from the beginning ICP research to company research all the way to proposal creation negoti you name it and everything in between okay so there's some really really good use cases in here that you could leverage for
that now one of the other areas that I wanted to point out is this is a this is an area so i' I've trained hundreds of people on how to do this Executives leaders Revenue teams and whatnot and one of the things I'm saying is there's like five core mistakes that they make that give them crappy outputs okay so this is super simple and I would like I said 90 95% of people do not do this so if you do this you'll be better than 90 95% of people in terms of using it
number one is custom instructions often forgotten very simple you set that up not all tools have it chat BT does co-pilot does not Claude does with artifacts you could leverage that um those are a couple good tools Gemini does not to my knowledge unless they just had it with their new release okay the other new thing is creating a use case catalog or what I call a prompt library or prompt Matrix most people have that kind of buried in slack channels or teams channels and they're sharing with teams but they don't have a centralized repository so what happens is you have some individual contributors
that are using it and 90% of the team that aren't and you have somebody who's amazing at doing these things and creating Innovations but they're not being leveraged across the team okay so you want to have it in a centralized repository the next is iterative prompting does anybody know what I mean by iterative prompting at all it's literally one of my favorit okay so we got some AI savy folks in the front row Kyle knows it too he's he's he's raising his hand over there so all it is and this is one of the super coolest functions within chat gbt you have an output you highlight it there's a little
quote Mark at the top you tap that in there and then you keep asking questions and drilling down you're going to get levels above like normal areas okay next one is Frameworks how many people in here have and I know you you guys do in the background so can't raise your hand how many people have a sales background and were an operator before they became a founder or an exec leader in here raise your hand little bit okay so most of you know so here's one of the coolest things this will give you skills you don't have and
like I saw this as disrupting Consulting in what I was doing before which is why I lean so heavily into this um you guys have probably heard of medic Med piic all these different Challenger sales one of the biggest things is have it identify that framework or that methodology and then have it deconstruct and build out things for you from that this could work across marketing this could work across sales any different area and then the last but not least and I did this with Gary tan the CEO of Y combinator how many people would like
him to personally consult for you how how cool would that be right so one of the coolest things that you could do and maybe there's not a lot of fans I think I saw like three hands raised so maybe maybe it's the bootstraping in everybody they're just like ah screw why commentary we don't want that right so anyways you could literally tap into them and basically tell the tool to act like him um well here's what I would do I would do it in two steps one ask him to be what he is known for identified in the chat box whatever it is and explain
all his Frameworks tactics and tools that he uses so start from there and then use the iterative prompting and say okay this is my situation I'm a bootstrap startup I'm at one million in Revenue right I need to grow and you can do this with like Jason lkin too which is kind of cool so there's a lot of different areas that you could do or authors tap into that and then go deeper so you got to give your situation your Revenue number the problem you're facing and then you'll get one-on-one consultation from some of the smartest in the world okay so that's the other area
so here's some actual use cases and I I wanted to make this real for you so that you understood it so these are three use cases specific for sales one of the teams I worked with he closed a $30,000 deal because he not emotionally had chat gbt cover his objections that he got when he got submarined by a competitor from a pricing concession at the last minute okay so he basically took the objections he was getting an email and then put them in chat be and asked asked
him how he would respond to this objection this is what he was selling and kept sending the messages back and forth and he closed the deal all right the other one is on the partner side this partner rep basically took something that took two hours it took them a day and a half plus and another um in terms of partner research there's other areas as well so if we looking at marketing there's some really cool cross functional use cases for this so I had a situation at the top they were trying to get something out for an Olympic theme
security awareness training campaign and basically she said what they did is they ideated they all shared the thread internally in marketing and then they took that ideated thread sent it over to product product actually integrated it into their solution and then they launched the marketing campaign they did this all in a day and this would have taken them weeks they would have missed their window if they did that another thing is because they had deconstructed like it was a pre-built prompt I gave them for social they got 12 of them qls from a single post which was 10x what they had before which is pretty cool
once again this is one of the areas where wouldn't have had the time to get it out right so one of the feedbacks I got from a chief operating officer of a $30 million series C S company was Ryan one of the coolest things about this is basically it's getting stuff done that we would say oh yeah we'll get to it and it takes a couple hours whatever but they just do it in a couple minutes and those are things that are getting done that weren't happening in the past okay last but not least this is how you could look at it from a data side we identified how many people have a fully
staff revops person in here nobody okay Rev Ops Revenue operations okay usually for bigger companies if you have the teams package in chat gbt you could effectively mimic a full-time revops person and basically these were some of the insights that we created where basically able to close rates by 40% improve it increase deal size from 21k to 91k in the situation and attack the Enterprise segment we all did this by
exporting and enriching the CRM data that they had having a teams account so was Secure then leveraging it and getting those insights from it all right last but not least and most people ignore this but this is one of the most valuable things about people is they got to be happy to work for it and lack of Engagement is equals a lack of or I should say a decrease in ibida okay so one of the coolest things that a cro told me was that effectively everybody brought it up in their qbr every sales
rep or every member on their team about how excited they were because they had the investment made in them and they the company really was promoting the use of AI in the workplace if you don't do that the biggest danger is people are not going to use tools that you want and you're gonna have amazing Innovation happening right under your nose that you're not tapping into there was a guy that created seven gpts that the company didn't even know he created one right and he didn't want to share it with anybody because he thought their employer were going to tell them to work
more all right instead we promoted him and what he did in that got excited and then effectively basically he started to share more and bring up the whole level of the team because of that right all right last we're going to go home because we only got a minute and 49 left so I'm going to cruise to this okay so this is how I would do it this is the foundation so I would do what's called a pre-print survey so what you want to do with that this is the exact process I I do so I'm I'm giving you everything here the pre-print survey is like what are
the most repetitive use cases what are their biggest challenges how do they want to make improvements what do they wish AI could do for them that they're not doing today get that feedback and then step one is you got to have the ire leadership team on board and they need to understand what's possible okay the other thing that I would do is I would do a combination of have someone basically take the lead on it if you're doing this internally if you need someone like me I can do this as well do that and train initially and then do a hackathon the following week where you collaborate in groups and share Innovations do it at the leadership
level first because they have to know it they cannot delegate right this is everybody it doesn't need just be go to market this to be development R&D um Tech doesn't matter okay then you do it with your team right I told you how to prioritize those areas then you do it with the team transformation and my recognition for a recommendation for a Cadence is like basically once a week training hackathon training hackathon training hackathon right so it becomes a habit just like working out right recognize those people that did really well and then do a post Sprint survey
after that you could do it over a couple month period so you could see the measurable results and then track what the outcomes are share those with the team and then promote them okay so that's idea dat activation now this is how you keep the flywheel once you activate this is how you keep it going on an ongoing basis you keep looking and attaching it to okrs you cultivate that that sharing internally you drive internal Innovation right you have monthly model updates because like I'm telling you some of these new updates are crazy on what's going to happen and
they're going to completely disrupt businesses and if you ignore them you are very subject to that possibly happening to you or you could be on the front side and ignore or disrupt other people I should always say right acknowledge and promote the successes so they keep sharing and then you track where you're at on the AI maturity index which I didn't even get to yet right so that's where you could scale it all right so just to wrap it up that goes from an idea to unfair Advantage you get the foundation the activation in place then what you do is you have that
ongoing process with your team and make it a part of your DNA and create that from an initiative to an unfair Advantage um this does work Jazelle who is a c or I should say a revenue leader say basically 10x what she was doing Russell loved the opportunity he was the one who told me about the qbrs with this team and last but not least iel he just attended one one session with one hour of of something I was doing it saved him three to four hours a week and said basically it it helped give him more
time to spend with his kids all right and that means a lot to people if you giving them that so that's pretty much it so last 20 minutes Ro I and AI activate it and then innovate we got what one minute for questions or I have no no time for questions no time okay I'm out I'm out but you can grab me afterwards if you want thanks [Applause]
