Empower Your Business with Sales Document Automation in UAE

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hey folks with us today Kyle from proposify Super episode thanks Nicholas happy to be here awesome let's start with the most important thing what problem does proposify solve for its customers problem we solved is when a company is growing uh their sales force they typically get into a a position where they start to lose control over the documents that sales reps are sending out so typically Pro proposals quote contracts um will go at the door they usually have some sort of approval process in place but it just becomes very chaotic managing it through work yes and so sometimes deals go out with the wrong information or the wrong pricing terms sort of thing so usually they'll look at proposify when they are growing their sales team and they need to get more control and more visibility into what sales reps are sending out to their prospects that's what we solve and is there a specific industry that has like the biggest paid in debt or are you quite Broad in terms of the industries you serve were quite broad we serve a number of Industries although the ones that we tend to have the most volume of customers within tend to be Services businesses uh we kind of break them into blue color and white collar so think IT consulting development sometimes marketing agencies would be that white collar service but then on the blue collar side a lot of uh franchises a lot of B2B franchises that maybe do like contractor work Landscaping parking lot maintenance anything where they'll send trucks out to a home yeah and then on the scale from like Mom and Pop shop and SMB to midmark to Enterprise where where do you usually sit in there we we started out serving very small customers and that was how we found initial product Market fit was through a marketing very small digital marketing agencies but over the years we've moved up market and now our Target customers more on the larger size so we serve you know large smbs mid-market and some Enterprises we'll use uh we'll use proposify and that's kind of more the direction we're heading I love that and I would love to dig deeper of that because you're nine years initial so you have tons of learnings on who to go to go after how to go after those people would you start with the lower end of the market at the smaller companies again if you would do it all over or would you go right after the Enterprise the Fantastic question and I think there's a lot there it's generally easier to Target small customers at the beginning because they are more open to trying new tools that are unproven that are buggy or don't have all the features so they're very fast to acquire and typically quite easy to acquire especially if the price point is low that starts to catch up with you over time because those same customers that are fast to switch will switch to something else or free tools or you know as your category starts to grow more more competition will come out so that's typically once churn becomes a problem and you only really notice churn becoming a problem after the first few million in Revenue very easy to ignore it in the early days but it starts to really catch up with you and compound later on that's typically where SAS companies try to move on market and I think there's a lot of learnings we could dig into if you like on how to move on market and how to figure out that Enterprise play or that sales oh but the other the flip side of it is starting out Enterprise or starting out serving very big companies and that's an approach that can work too I personally haven't tried that but what's working against most companies if they try to start out Enterprise is just simply the lack of stability Integrations privacy security and all those types of things that enterprises want to see and they want to see a proven track record so that that becomes challenging I think that there could be a case to be made if you have come from a very large Enterprise and you're starting a SAS business knowing exactly the problem and the Ping points that you solve and being able to say hey look I've lived in these shoes I've been a corporate VP at a you know 10 000 person company and I know exactly what problem to solve sure go out and build that solution because you know what it is but if you if you haven't walked in those shoes it's going to be hard to sell it yeah yeah I feel like it's a for a lot of companies like the natural progression to to get bigger clients as they get bigger themselves and I I would love to really dig into it because you you mentioned the the transition how how big were you in terms of both Revenue like roughly and uh head count when you made the the switch to a let's try to go after the bigger fish now it was a very slow Progressive transition so it's hard to say exactly where we were at but I want to say we were at about couple of million in Revenue when we started to just experiment with higher price points and to hire our first sales rep reps that would have been around 2016. that there's a lot of stuff we didn't know and so it was very experimental it wasn't we we hadn't made the decision oh we're going to transition towards Enterprise it was very much a hey let's play around with this and see if there's something there uh we had more or less copied base Camp's price point they were selling they had a 3000 a year plan they were selling we tried that and again we sold a couple of them and we thought at the time that those were very big customers wow 3 000 a year we were used to selling 20 a month customers but um it was it was interesting where it went because we were able to eventually close customers that you know some now pay us six figures or more but that was very gradual and there was a lot of pain and a lot of stumbling along the way to get there do you feel like it was the right decision to start rather small in terms of the the price and very experimental instead of making maybe not the rational but like the more trying to plan ahead approach of saying now we're going after the Enterprise let's chase six figure deals I think it's the right approach to start small and experiment especially if you have an engine that was that's working right and we had we had a lot of really good growth from small customers our self-service sort of product LED growth engine was very very sticky and and it was that was where our growth was coming from that's the right time to experiment with another Channel or another customer segment the approach I would take would be different next time and I wouldn't hire sales people off the bat I would do the sales myself me and my co-founder probably could have done that for a year to experiment rather than outside reps in trying to train them on a sales process or a sales motion that we really had no experience running ourselves so I would do that differently and I think through the course of doing that we would have discovered some of the objections that you face when you get these bigger customers on calls like you know how how does your sales force integration work and how you know do you guys have sock 2 compliance do you have single sign-on like all these types of like security privacy type of requirements at that stage we would have faced those as the founders and that would have helped inform the product more um I think the way we did it was just slower it just took there was there was too many layers in between us and the customer and so we didn't learn as quickly as we could have at that point why did you not make the decision to to do it yourself because I I guess you you had the thought in your mind back then so for the founder listening who's in that position right now he wants to go the direction buddy was it more like oh no I I don't have time or I hate sales like what made you not do it and like why do why do you regret it now both of those reasons you you mentioned don't have time and I hate sales but I think there's more to it than that so I actually don't hate sales but sales is is a grind and it is time consuming and there's a lot of rejection especially if we're doing kind of outbound prospecting which we try to do a little bit of um that just takes a long time and so when things are working and and growth is good and the team's growing and we're just busy with other things very easy and very tempting to just want to Outsource that let's bring somebody in let them do it they've got the time the hours to put into it I think fundamentally though it is a mistake and yeah I think uh it's you're denying yourself the the first hand knowledge and learning that you could you could get and also it's just expensive to bring sales people on who can't close deals who you're you know you're paying them a base salary but obviously if they're not hitting numbers consistently they're not happy it's much better for everybody if you as the founder have said okay for the last six months I've been taking three days or two days um a week to focus on sales to bring in some higher ticket prospects and through the course of doing that we've learned where we fall short in terms of product where maybe our positioning should change or just how to price it because our pricing was limiting us to just the metric that we were pricing by was limiting the ability to sell six figure deals with that knowledge and with some customers that we were able to successfully close we could have at that point brought it brought in sales reps and said hey Shadow us for X number of weeks watch us do it take some calls yourselves we'll coach you and train you and then get one or two reps closing deals and then at that point if it's working if you can get some outside wraps to close because you figure it out you've at least built a foundation for them to be somewhat successful with then that's the point where you want to bring in say a head of sales VP to to build the team and grow it you don't want to do that early on when you have anything figured out how to close big deals and that's the mistake that I see a lot of SAS Founders want to make I coach a couple of SAS Founders as well and you know I see them fall into that trap as well I need a head of sales how many customers do you close none you know they're not going to figure that out for you yeah right head of sales come in and they build they take the engine that's there and they get it faster and hotter and they grow the team they train they coach reps they don't figure out product Market fit they don't figure out your positioning or fix your product for you and so then what size Founders do is they bring in ahead of sales they can't make their team successful and then they get rid of them in 12 to 18 months and golf now I tried sales it doesn't work that makes makes a ton of sense so in summary doing founder let sales basically learning the ropes making the rough mistakes making the adjustments bringing in the first two reps and when they're successful then bring in the the leadership layer correct correct that's it's an approach that's been proven to work if you need to hire the right developers and ship fast then react Squad is for you a boutique agency that specializes in react and only works with fast growth startups they have 14 day risk-free trial and a transparent price of 95 dollars per hour visit reactsquad.io to learn more how does your sales for right now are you roughly 60 employees or how big is the company right now yeah we're about 60. how many of those are in the sales org uh today we have with us today um four AES account Executives who close and then we have two bdrs and then we have a director of sales kind of and then the uh the bdrs basically setting appointments for the AE so it's like two AE share one bdr or how how does that uh make it like the Mechanics Work of that sales engine we've structured this a few different ways but last year we made a change and we actually had the bdrs reported into marketing so Nadia is our VP of marketing interesting overseas and coaches the bdrs and they essentially handle all the inbound leads so when somebody requests a demo through the website the bdrs will will jump on that first call run some basic Discovery and then if they see there's a good fit they'll set the appointment for the AE and that actually has has worked well for us I don't think there's a one-size-fits-all answer to that and I think there's certainly pros and cons of having beat errors reporting to marketing versus sales but for us it seems to be working and what it has helped with is created a very tight feedback loop between people sort of on the ground floor talking to prospects feeding that information back to marketing to say these leads are no good we can't help them they're too big they're too small they don't understand what we do whenever it happens to be they provide that feedback to marketing who can then tighten and refine the messaging of what we're putting out there in terms of campaigns hunt and then has I guess sales has a quota but does marketing app or at least marketing leaders who have like some kind of quota in terms of how many qualified leads they have to push to sales monthly or quarterly yeah marketing has a pipeline quota so we don't do it in terms of number of leads because lead you know size and quality can vary we also score leads maybe a Sit B set so marketing instead has a pipeline that they're able to hit and generally speaking it's about five times what sales quota is so you want about five times the quota coverage in terms of pipeline and then because you you briefly mentioned before that you tried out but so did you try out bomb versus SEO versus some other channel and then it just ended up being involved or like how did you end up on being inbound driven at least if I understood that correctly tell us a bit about the on the other part of basically how do the bdrs get their leads and how how did that evolve historically yeah I mean if we go way back to when we hired our first reps um we hired a third rep Scott who's um funny enough now our director of sales he's been with us that long and he you know he was doing a lot of prospecting and open we didn't have a process figured out for it though and it took us a long time to sort of figure what that is but um we haven't given up on it we still do a fair amount of outbound we what we found at least lately is that the AES do the majority of the outbound um bdrs a little bit but it tends to stay mostly with the AE so essentially in Scott's been a big proponent and a big believer in outbound for as long really he's as he's been with us so he encourages the AES and and leads by example in terms of just making sure that every day or every week we're doing some kind of outbound prospecting activity it doesn't necessarily Drive the pipeline about 20 of the deals that we close come from outbound but 80 come from inbound so the inbound engine is still the one that's providing the majority of the pipeline and the majority of the value now that said outbound can work it does work um I wouldn't say we've gotten it down to a science where we could just say plug in 100 years produce quota for us the way a lot of SAS Founders would like it to be but what we do find is that the deals that we close from outbound tend to be larger so if you if you are going to close that big whale of a customer they you know it's more of a 50 50 split so they tend to lean more on the bigger end so there is basically take the yeah let's say capacity they have for outbound to really go like elephant and whale hunting in a way yeah absolutely but it's still even when you do that you're likely not going to land a massive customer at least right off the bat usually there tends to be some kind of proof of concept or they sell it to one division within the company or one team and land and expand has been the approach that's worked well for us and I know works for a lot of SAS companies is you bring in a company maybe it's a 10 seat deal or a 20 seat deal but you know that there's a capacity for 300 500. and really that's where the the partnership between customer success and sales comes in because this customer success manager takes that 10-seat deal and over time nurtures it and grows it into that 300 seat deal the last time I asked that I promised does CS also have a quota in terms of upsells or is customer success basically like quotes a list in a way no they have a quota they have expansion targets so their job is to expand or retain a certain amount of net MRI churn or a certain amount of net MRI retention so as a whole we're aiming for about 120 percent in terms of Revenue retention annually so that would just break down for the CSM you know how big is their their book of business their job is to keep a hundred percent of it and grow it by 20 annually and so then that breaks into quarterly targets makes sense so if we look at a high level it would be the marketing department delivering pipeline so potential Revenue the sales department closing new new mrr new revenue and then the customer success Department making sure that Revenue base grows you've got it yeah per se and then I would love to switch gears a bit from the let's say in the business platform of like the the being a Founder file you you're edit for nine years now and I see like a lot of Founders get like itchy after five or six years to do something else how do you feel about that and what if you have that urge to like play around with other things how do you integrate that into your job as a CEO to to keep being focused while scratching that itch basically I'm really glad you asked that question I think it's an important topic one that maybe doesn't get talked about enough uh you know at nine years in my previous business I had for five almost six years so I'm I tend to be one of those Founders who stays around a long time running a business I'm not a hey every year or two I need to flip whatever I'm doing and sell it to somebody and go start up again now that said I I mean I'm a I can imagine that is very similar to like you know musicians that have been in bands for a long time 10 20 years you know the Rolling Stones if you will um there they've got to get itching to try something else to do a side project to do a sideband but they always kind of come back to their their main you know their main band that's kind of how I feel about proposify definitely have gone through periods of time where I've felt frustrated towards just wanted to sell it and move on and do other things um but I think the I think the important thing there is for any Founders that are listening to this if you can see if you can look at what you tried to accomplish initially so when you started your business maybe you were in my case it was trying to get proposal software created you know trying to get that off the ground have customers using it never you know almost didn't think I would get to a million in revenue and here we are 10 million and going ah is that all like we shouldn't be able to be even much bigger than that but I think as long as you can keep challenging yourself and challenging your vision to say okay we did this it works good now how much what else could we do that's even more ambitious and more crazy if you will so I think there's ways to almost create a startup within your existing business and I would encourage a lot of founders to to really think about that because the thing is unless you happen to be one of those Maniacs who just loves to be in startup Grind Mode all the time let's face it it's not a fun world to live in right you don't have any money you have no team you have to do everything every it's it's unproven what you're doing like you don't have any real evidence that people want whatever it is you're trying to build whereas if you can create a startup within your existing company that already has a revenue and it has an opposite Finance team and it has all the infrastructure in place to feed yourself feed your you know family need to be able to afford great lifestyle but then you can go cool now I want to build a new product within it or I want to build a new service or I just want to take our existing product vision and 10x it and make it you know way more ambitious that's a better place to be in and and even from a wealth building perspective you're more likely to be successful doing one thing for a very long period of time then you will be trying to do a new business every two or three years or even every five years it's just it's just a slower way to make money honestly did you have to play some let's say mental games or they'll do a bit of mental gymnastics to get to that place or was that just the way you want your wired basically and that's how you ended up sticking it out yeah I did have to do mental gymnastics to get there I wrestled with it for a long time and and I even you know seriously considered and went down the road of looking to sell the business um now two years ago that would have been probably a fantastic idea because valuations were very frothy and even moderately performing businesses could command huge multiples if they were SAS by the time I was considering this the market had changed significantly valuations were down you know the the we were we were entering a recession and so suddenly it became less of a viable exit strategy um so in some ways I'm quite glad that that was the case because essentially I thought I had a door out and the doors closed that was not an option so I was really left with only one option which is keep doing this and in fact do it 10 times better than it's going or or 10 times the more ambitious a vision or 10 times better in terms of performance and growth so in a way it was kind of a blessing in disguise it was like you only have one option and it's through there's no way around it and I hint I think for other people they may not be in that situation um so there might be some mental gymnastics involved but I think it it may take a lot of time and a lot of reflection to be able to say to yourself is quitting or is basically trying to find a buyer for my business and trying to cash out really what I want to do um because for anybody who's had cash windfalls before whether it was selling shares or or selling previous businesses you kind of realize that once that initial period of of excitement wears off of like cool I've got a lot of money in my bank account and I can afford a fancy car or I can pay off my house once that goes away you're kind of left with okay what do I do now and I mean this has been pretty well documented that the majority of entrepreneurs who sell their businesses end up depressed within the first year afterwards and and so I think yeah taking that into consideration and going why do I really want to sell it now is it because now is the best time for the business because maybe we could partner with some bigger strategic firm and become much more really fulfill the vision in a much bigger way um typically it tends to be like Oh I'm just you know things are hard I hate my employees I hate you know I hate where we're at heart you know we're stuck um but the thing is those are always going to be true and so what I did was I kind of thought to myself like part of my personal vision is to become an investor and you know I've done some Angel Investing but I would like to have a portfolio of businesses in SAS in some other Industries when I looked at it and I said okay so what do I want to do one day it's to take businesses that are struggling to grow and to sort of run my playbooks through them and get them to that next level well if I can't even do that for myself I can't even do that for my sole business how am I ever going to learn how to do that for other businesses so that was part of the mental gymnastics I went through I love the honesty and then because we were running out on time what's that 10x Vision you came up with I want to hold that close to my chest right now um but I will say that when I look at what purpose if I can be in five years we've seen the power that generative AI has had on many SAS businesses in just I think SAS in general um probably the greatest technical Revolution that we've seen since smartphones since the internet um that is very much what the vision is rooted in and really practical ways that AI can be leveraged to create much more robust automation for documents at scale I love that and then I'm already looking forward to seeing what that ends up being when it's even more concrete yeah I will be sharing it this year amazing uh I will I will keep stalking you to make sure I don't miss it and then one final thing if people want to reach out either to you or to proposify where can you be found online sure so you know obviously if people want to check out the software they can it's proposify.com for SAS Founders who are listening some of the content that might be more applicable for them is just my personal website kyleraki.com so that's r-a-c-k-i it's Rocky um actually a Croatian name my great-grandparents came from Yugoslavia for those that are interested I only say because you're European um but yeah no I have a personal website where I have a new a Weekly Newsletter I share some of what I've learned over the years running a SAS business that's very applicable to SAS founder so if people wanted to check out kylerackie.com they can sign up for the newsletter and share content like this perfect and I will be sure to link it up for everyone Kyle thanks again for coming on thank you Nicholas I really enjoyed you have me if you like this episode then you'll love the SAS operator a Weekly Newsletter brought to you by early node with actionable insights from SAS experts in the industry delivered right to your inbox every Tuesday for free visit earlynode.com to subscribe