The Future of Sales: Authentic at Scale

Scheduled for: December 10th, 2018, 3:00 pm PT / Category: Interviews

Matthew Bellows will share with us his advice on how to have sales conversations that are Authentic at Scale.

Matthew Bellows is Founder and Board Chair of Yesware. He was CEO for the first eight years of the company’s life. Yesware is the leader in sales productivity, serving over 60,000 salespeople at companies like Box,, Twilio and Yelp.

Prior to Yesware, Matthew was the Vice President of Sales at Vivox. Before that, he served as General Manager at Floodgate (acquired by Zynga), as Founder/CEO of WGR Media (acquired by CNET Networks), and as VP Sales and Marketing of Interstep (acquired by Flycast/CMGI). He earned his B.A from Naropa University and his M.B.A. magna cum laude from The Olin School for Business at Babson College.



Dulce: Hello everyone and welcome to a new edition of DojoLive connecting tech experts like you, into this edition we’re gonna have a very interesting topic and a very special guest but first, my name is Dulce and I’m broadcasting live from Hermosillo and also we have our very special co-host, we have Tullio Siragusa from Los Angeles, hi Tullio.

Tullio: Hi Dulce, hi everyone.

Dulce: And we also have Carlos Ponce from Mexico City, hi Carlos.

Carlos: Hi there, good to have you here Dulce.

Dulce: And we have Mariel from Chihuahua she’s gonna be joining us today for the first time in DojoLive, so welcome Mariel.

Mariel: Hi, thank you.

Dulce: So now, yeah.

Carlos: No no, I said cool, go ahead.

Dulce: Ok, we’re gonna introduce or today, our, very special guest today which is Matthew Bellow he is the founder and board chair of Yesware, Yesware is on all in sales technology to get used by enterprises and for half million people around the world, so thank you Matthew for joining us today, hope you have a lot of fun with us today, we’re gonna be asking you questions and knowing more about you and your company so before we talk about today’s topic I would like for you to introduce to our audience Matthew just a couple of words before the topic.

Matthew: Alright, thank you very much for having me it’s a pleasure to be here on DojoLive it’s great to be here, and I’m looking forward to the conversation, I’m Matthew Bellows, I’m as you said the founder and currently the board chair of Yesware until this August for the first eight years of the company I was the CEO of Yesware and just recently promoted our CEO to be CEO so happy to talk about that transition or what it’s like to bootstrap a company our first company was bootstrapped or raise money for company Yesware venture backed or whatever else is on your mind today.

Mariel: Awesome, so well today’s topic you choose the future of sales authentic at scale, why did you choose this topic?

Matthew: So I have been a salesperson for most of my career both as a quota carrying bag carrying sales rep and also as a sales leader, and as a CEO you’re sort of the chief salesperson of a company anyway and so over the many years of doing sales and you can tell because my hair is getting shorter it’s been many years, you know, that the challenge is alyas how do you, how do you connect with people, how do you communicate with people how do you build authentic relationships with people, in order to see if there’s mutual business opportunity there, that independent what sales is but there’s a need to grow and the need to grow faster and there are ways to apply technology to that problem like yes where it does, and so there’s this natural tension between being authentic and communicating enough to get enough interest to grow your business and so I wanted to talk about that tension and particularly how the combination or a certain approach to software can help solve that problem.

Dulce: Oh great.

Tullio: That’s great, I’m very curious to get right into it Dulce, so been in sales marketing strategy for the almost 30 years, so totally in the state of my hair is getting short too, and you’re right I mean it is all about having authentic memorable conversations where you’re not just sending like another me to, hey would you like to do business with us, and that how it’s a challenge and there’s different things we’ve done so I’m curious from your perspective what was that moment where you say you know what I’ve got an idea and I got to bring this out there because this works what gave birth you Yesware.

Matthew: Well the inspiration originally for Yesware was that I was a sales VP running a small sales team closing big deals very infrequently and yet every three months I had to stand up in front of my board and I had to say you know, here’s what we’re gonna close next quarter, here’s my thirty sixty ninety day pipeline, and so the process of putting that slide together was a complete nightmare right I was talking to the sales rep, talking to the prospects trying to sort of measure and guess what where these deals where and what they’re actually gonna come in and it justs felt very very much like throwing darts at a dartboard as opposed to you know, a science of measuring where things actually where. And so I was seeking the data for the sales process and it turns out that a lot of the data is already in email and calendar and so I thought how do we integrate software into email and calendar such we can get access to that data so that’s not really particularly about authentic at scale that’s really about trying to understand the underlying activity data behind sales and marketing and customer support and success from the unstructured data that’s there but where we got to very quickly was once we realized, hey if we help salespeople do their job better then they’re gonna make more money and if they make more money they’re going to give us some of it so we’re gonna have a company if they give us some of it there’s going to be this constant pressure to automate automate automate which you know, which I think we’ve seen where the number of b2b spam emails are up the number of like generic email blast that go out are up the number of robo calls that go out you know, to your cell phone or your home phone at dinner time or up and all of this isn’t fundamentally unsatisfying and actually damaging to people’s brandman careers so the question then became well how do we apply technology appropriately to this problem so that salespeople can be more successful and make more money without destroying their reputation their company’s brand and the prospects in you know, attention span.

Tullio: Ok, so that’s first of all I have to acknowledge that it’s rare to hear someone actually talk about I didn’t acknowledge our salespeople what I call coin.4-operated, you got coins in the machine right so it’s refreshing to hear a founder say if they make money then we’ll share some of that with us so from that perspective that you’ve just got a fan or sure.

Matthew: Ok, good, all right.

Tullio: So just help us understand if you don’t mind, you know, how does it actually help a salesperson be more productive or more effective what are some of the capabilities that the software bring to bear.

Matthew: Sure, sure, so I mean the first thing I would say is you know, I’m gonna tell you some things but the best way for you to understand this is just to experience it and so the way that we make that easy is we say go to Y E S W A R E .COM and just download the free trial and install it in your Outlook or in your Gmail and see if it works for you, now we have put a lot of effort into making sure you don’t need to read a lot of manuals and go to training classes and do all that stuff to get value out of it but you know, the real things is going to be for you, does it work, but I’ll give you a preview of your experience and tell you some of the ghints you’re gonna experience although there’s too many features too like list them all, the first, the first feature that we really hit it with, the feature that we build that actually made salespeople light up was basically email analytics, so I believe we where the first company to add email tracking to one-to-one emails and what that means is that when you install our software into your email box and you send an email to a prospect you see that they opened the email and you see that they are located in a certain you know, geographical area, you see the platform that they’re on so if they’re checking their cell phone as opposed to answering on their desktop computer you can even see sometimes like do they click a link, do they download a document, do they read num slide number five for five minutes, there’s a tremendous amount of insight that we give to the salesperson to understand how their prospects are interacting with their messages and what’s really the sort of first “aha” moment that happens when people try Yesware, they’re like: Oh suddenly I know this person is interested they’re coming back to my message they’re downloading my proposal etc etc, as opposed to a they’re not interested I’m just gonna leave them alone.

Tullio: Ok, so if I’ve got an account-based marketing strategy I’ve got a lead a team, I can essentially what you’re saying begin to score the quality of an opportunity based on the interaction they have or lack thereof an interaction that can I then learn based on that like, where there’s more likely to get better conversion, people open it on their mobile phone or on their desktop or from home or from the office, what are some of those insights that can help if your sales need to really get better about how to tackle the marketplace.

Matthew: So we just posted a new free website which is all about what time to send your email, because time and the time that you send it actually has a tremendous impact on whether it’s going to get open and whether it’s going to get replied to, and based on your location and your prospect location that really matters, so we’ll put a link in the show notes to this new tool but that would be one example of if you’re based in Mexico City, and you’re selling to someone in New York City, what would be the optimum time to send that mail and then we have technology that allow you to queue it up to be sent at that time as opposed to you know, you having to stay up until 3:00 in the morning to send it at midnight in New York time or whatever it is.

Tullio: Ok, so it takes into consideration that sometimes sales guys forget to put things on their calendar to follow up.

Matthew: Sometimes [INAUDIBLE] there’s a hole, yeah I know, there’s a hole.

Carlos: I’m sorry, I’m sorry, Tullio we have a question coming in from, from, from someone of the team actually, can I sep in real quick, ok, we have a question actually she’s one of her teammates and this is from Sandra Vasquez and Sandra thank you Sandra for watching and also for asking your question, so Matthew, Sandra one of our teammates from the sales and marketing team, she’s asking, just put my on my glasses here, and she’s , this is, what this is her question, she says: Customer success isn’t just measured in transactions but in the lifetime and network value of each business relationship in a “spam filled business world” you know, how would you say that Yesware contributes to this?

Matthew: Contributed to building the genuine relationships in the long term.

Carlos: In the lifetime in the network value of each business relationship.

Matthew: So that is an awesome question and that applies I think both to sales people and to customer support people end to BTRs and you you know, any basically externally facing professional so the essence of it and the essence of authentic at scale is to apply technology such that you can be personal, be relevant be knowledgeable about the other recipients of your message and still communicate effectively often enough and quickly enough and efficiently enough that you know, you could hit your numbers, so a whole big feature set of Yesware is about integrating data sources from other places on the web to put it right where you’re already doing your work, so for example we have an integration with LinkedIn I can show it to you, if I do, do you mind if I share my screen?

Carlos: No we don’t mind at all, you can actually doodle it show it to the camera.

Matthew: Screen share, if I, I share if share my screen will the camera pick it up, all right so ok, so here we are, you can see my gmail now.

Carlos: Yes.

Tullio: Just expand it if you don’t mind.

Carlos: Hold on one second.

Matthew: So what you see here is my gmail interface with the Yesware functionality built into it, you can see this bar across the top which gas these different features into it and I’m not going to go into all of them because it would take too long, but to this point, you can see this tab is my Salesforce integration so all of my Salesforce data can go here and if you where in, if Carlos was an existing lead over contact in Salesforce, all that data would be pulled out of Salesforce and displayed here, similarly here’s our LinkedIn integration so here’s your LinkedIn page and I can save that to sales navigator I can read more about it, I can see all your connections, I could see are for shared connections, I can see relatedly [INAUDIBLE] etc, so that when we’re calling it’s very easy for me to go here and be and make sure the information that you and I talked about is relevant, I can see your background etc, we’re trying to place all this stuff right in the, in the workflow of the sales or customer success professional does that make sense.

Tullio: Yeah, I’m loving this.

Matthew: I want to, I want to just see if I can go.

Tullio: What on the platform integrates with Matthew is it just Salesforce or like HubSpot and other or that on the row map.

Matthew: So it integrates with Salesforce, at an API level and LinkedIn at an API level and then it also integrates with most other CRMs at sort of at simple but easier to use level.

Tullio: Ok, so if my email is integrated for example with Hubspot it automatically would by nature integrate with that somehow.

Matthew: Yeah, you can set it up and we have online tutorials to send your emails in this into Hubspot from Yesware, but we were talking earlier if you don’t mind that you are saying like sales people forget what is they’re supposed to do next.

Tullio: I mean there’s a study does like seventy percent of the opportunities just died because people didn’t follow through, I can’t tell many times, I got a LinkedIn contact give the person an email and phone number, never hear from them like I just I was just there for you to go and follow up with me [INAUDIBLE]

Matthew: And isn’t interesting I mean that’s if you get, if you get, if you start talking more to the people who actually want to talk to you then you don’t have to spam as much, because you’re reaching out people who are already want to be engaged with you so we have this feature set called campaigns which enables you as an individual salesperson to put together your sales methodology and i’m not going to go through the whole thing but what it does is basically say if you have a sales approach that says first your research the lead, then you send a particular introductory email with relevant value added points then if you don’t hear back form in three days you call them and here’s the script that you say, etc etc etc, you can stretch that out and have a whole you know, fifty touch campaign or ten touch campaign, what that all results in is just as very easy to do lists, so you can see here’s my there, I sent this email he was out of office at the time, I’ve got to reschedule this email because he was not there, he was on the plane out of office, then my next to do, so I’m gonna say skip this touch, my next action is I‘m gonna keep in touch with Glenn Stanford and I’m going to check his check news on it’s company because the next thing for next best thing for me to do is research this lead, and then I’m going to snooze that because I don’t feel like talking to Glenn right now instead I’m going to talk to Nepal, etc etc etc, like I have now a smart to-do list that helps the salesperson keep up to speed with all the tasks on their list and then, and then tell them what’s most effective and what’s not, there’s a ton of stuff with it yes we’re so again this is like a little scratch the surface thing but I’m totally resonated with what you’re saying about it how hard is for salespeople to keep on top of all the differents task they do, especially when they’re trying to operate at scale.

Tullio: Yeah, absolutely I mean, this is very time for us as well, we’re looking at this stuff that’s just offline conversation with that I’m very interested but I’d the other question I had, is you know, one of the challenge is always trying to institutionalize what’s working well right, we recently ourselves did a force field hose to really look at what we do very well and where are the gaps and you know, there’s always pockets of information and either someone’s ability email or the way that they approach something and as a Sales leader it’s always the biggest challenge like how do I scrap you know, extract that insight in those gems and institutionalize them across the team, is our the insight social looking for things that are scoring well that are getting good response and then could I look at that and say ok, this is the stuff that’s working that we should try to like do across the board, can you tell a little bit more instruct on that.

Matthew: Yeah, it’s absolutely it’s a huge point, so if you think about you know, a team of 10 salespeople they all have some similarities and some differences, but fundamentally they’re all, they’re all doing their thing in your sales process more or less to try to close more business that’s actually like 10 little scientist out there experimenting trying to see what’s working or not, and so what we do with in Yesware is we measure not only the activity how many times did they send an email and things like that but also the response, the result, how many times did a user open an email to click a link to and most importantly did they reply, and then we can associate those results with the messaging what the salesperson sent and then we can say to the team manager: Hey of your 10 people this is the best, you know, prospecting email template out there, like this prospecting email gets more opens with this subject line and more replies with this content than anyone else roll this out to your whole team and the thing I love best about it is when the marketing people come out and they’re like: Hi wait that’s our job, our job is to come up with the great language and that and the messaging to get the word out and we just say: Great let’s test them both, let’s put both templates in there and let’s have the team split up or send half and a half and see which one works better so it’s very data-driven approach to finding out what works.

Tullio: Sound like a dream come true, I mean you know how much time you in the spending analysing, looking for information instead of actually helping the team going out there and getting more effective it just has to be done it’s all manual, tell us a little about adoption, our people jump I mean people should be jumping on this, I don’t, this is, I’m excited, so I’m pretty sure everybody Carlos was excited to try too, but tell us will be about traction, you’re getting in a marketplace, what are some of the hurdles you facing, how’s the, how’s it’s going.

Matthew: Yeah, I mean it’s first I’ll say to you and all your fans and listeners they know, like it’s not easy building a software company you kwno, it’s a there’s always challenges there’s always things going wrong, but yeah, the response has been really really encouraging, we’ve been at it for eight years, over a million people have downloaded and used Yesware, we have you know, then of thousands of 60 or 70 thousand you know, daily active users of guess where we have thousand of seats at some very big publicly held companies like Twitter and Yelp and Box, and many others we also have lots and lots of very small businesses and individual salespeople agents and real estate agents and PR agents and people across the spectrum that use Yesware every single day so it’s really as a you know, as a salesperson myself it so gratifying to you know, have worked hard to you know, build a software tool that actually helped a person do their job better.

Tullio: Yeah, that’s pretty amazing, any stats you can share in terms of before and after improvements in you know, conversion or engagement anything like that you guys track that you gather.

Matthew: Well, we’ve worked with a number of our customers to try to figure out where it moves the needle, and some of the places where it’s really our customers have reported really be more effective after using Yesware is in time to connect so one customer did a study and realize that because if you train your sales team to reply when someone opens their email like to reach out to them when they’re reading you message, you get about a 30% improved connection rate, which is a huge huge gain when you’re trying to find it you know time when you’re you can both talk about something, we’ve had you know, we save our customers an average of 1.5 hours a day in entering your data into your CRM we basically take all that sales data entry stuff off the table and that gives sales people you know, another 20 or 30 percent time to sell, every day, so they don’t need to data entry and it means that the companies that you know, employ their sales people get access the tremendous amount of additional data they never really had before so there’s a, there’s a number of easy ways to tell the ROI story for us we’re actually that has not been as much of the problem.

Carlos: Tullio, sorry for interrupting we have another question.

Tullio: Go ahead.

Carlos: Actually this question is coming from our very own Fausto by the way Tullio, you know, our numbers guy is all things data analytics right, so what’s Fausto was asking is a question for Matthew of course, but he’s asking: In the sales software space how would you say the things like gamification and real time data visualization increase transparency and awareness of the activities that matter most to revenue growth and success.

Matthew: Wow that’s a really good question, so I my first startup was in the video games industry so I’m very and I love video games I play ok, thought I’m very aware and interested in the whole aspect of gamification of enterprise software or you know, for business users I would say, I have know a number of very focused gamification companies that have sort of wrapped rows and fall over the years because they’re not adding enough business value they’re just sort of adding eye candy for four monitors and companies I think the real point of gamification is instead to kind of blend it seamlessly into the enterprise software so it’s that, it becomes a little more fun, but now necessarily like a you know, triple-a video game, in terms of real-time data thought I think that’s much more impactful because you know, what you like described how if someone’s opening your email that’s a great time to call them, that has to happen in real time, there’s not a lot of room for you know, five minute or twenty minute updates it has to happen immediately in order for it to really work, so we have built guess where from the beginning to be a real-time system and I notice now my screen is frozen so talking about what that means of [INAUDIBLE]

Carlos: We can still hear you.

Tullio: Well time is flying really fast, I’m super impressed with this, I’m definitely curious to check it out and learn more, I am, you know, you’re been at this for eight years and curious to hear what your journey been like as an intrapreneur kind of ubilt something you know, really actually you’re providing a value as a professional yourself as an sales professional self, for everybody else, what’s that journey been like for you if you don’t mint sharing that with us.

Matthew: I’d be happy to do, I mean it’s like I said, its , it’s not always up and to the right, and it’s often very personally challenging you know, what I find is that being you know, the CEO or being a leader at a company after challenges me in ways that I sort of didn’t expect it sort of reveals blind sports and reveals areas where I sort of don’t understand the impact of my behavior so although it’s been rewarding and helpful professionally, I would also say this time has been tremendously valuable just from our personal growth standpoint I feel like I’ve grown and learned a lot as a human being as well as you know as a business person so I wouldn’t trade it for anything, I think I’m kind of spoiled thought I don’t think I’m gonna have a hard time working for anybody else.

Tullio: Well you’ve built somethinig really fun and exciting so we’re happy to hear about it, we’re gonna definitely check it out, if you were looking from the outside in and you had to give yourself some advice, what would you have done differently early on.

Matthew: Oh my god how much time do we have?

Tullio: Usually you have any words of wisdom but I’ve answered it differently this time.

Matthew: Ok, so I mean the thing I think about that stuff a fair amount and the thing that I’m thinking most about now with regard to what I have learned from this experience is that especially at the onset it’s very very tempting to sort of dodge the question of what’s your target market because you know, certain I don’t want to predetermine it you sort of not really sure you know, you know you could build something and other people could like it and wouldn’t and Yesware we’d started Yesware that way, hey sales is a very big market it’s very dispersed who knows who’s gonna like it, let’s just build it for salespeople and you know, I think that’s and let the data determine you know, where our target market is and I you know, it’s hard to argue with what we’ve achived but on the other hand I think we would have been faster to this point if we had been more explicit even at risk of being wrong, about what our target market is, thought I would suggest that folks who are things about starting a company or in the early days of starting a company put your stake in the ground to say these are the exact kind of people companies, buyers ,personas, locations ages, demographics whatever it is, be very very narrow about the core target market that you’re aiming for to make them really happy, like I saw I read this awesome book by [INAUDIBLE] is the founder of black diamond and Patagonia, and his core target market is the dirtbag hikers, the hikers who really don’t try anything else they just want to get back in the mountains and they live their whole life and they organize their job and their clothes and their apartment and their car and their relationships and their pets and their girlfriends and boyfriends, all around getting back in the mountains, and that’s the core target for Patagonia, now if you buy Patagonia stuff you know that like you don’t have to be that person to love their stuff but he says if you can’t make them happy we’re not gonna make anyone else happy, and I just love that very distinct and clear target market so I wish that we have been a little more focused about that you know, six or seven years ago.

Tullio: Thanks that’s really great advice, it’s amazing how many companies especially software company develop an MVP but fail to look at the minimum viable segment of that MVP so that’s great lesson learned appreciate it, times always up when we’re having a good time, I gotta pass back to Carlos who might have a few announcements and then back to Dulce, it’s been a pleasure talking with you Matthew and I look to continuing our conversation offline for sure.

Carlos: Thank you so much everyone Matthew, just a quick announcement before we wrap it up with Dulce and this is about the next interview that we have scheduled for this week which is going to be on Wednesday next this Wednesday, at exactly 1pm Pacific and the conversation is going to be with the senior vice president of engineering of a company called it’s a platform called Amava which is a platform that enables post-career professionals to discover their next move, their next gig, so I think it’s a new vision for all people older people like myself and Tullio, but so we should look forward to have this conversation with KP Naidu the senior vice president of Amava and that’s gonna be again Wednesday at 1pm Pacific and the topic is going to be, let me just double check real quick and what the topic is going to be about and then I’ll fill you in, let’s see, ok, hold on one second, this is a little longer than expected because I need to pick it up, let’s see.

Tullio: Quickly Dulce tell a joke.

Dulce: My own name is a joke.

Carlos: The sweet [INAUDIBLE], this is for some reason, ok here’s the thing, the interview again, KP Naidu, senior vice president of engineering Amava we’re gonna be speaking, talking about managing an engineering team at a startup so that’s gonna be more relevant than that, lessons from the last three years of creating and nurturing a team of contract software engineers so I should be interesting, let’s say 1pm Pacific, stay tuned folks.

Dulce: Ok, so sadly we’re coming to an end for this edition of DojoLive we’re gonna say, thank you, we want to say thank you to Matthew for this great conversation hopefully we’ll see you next time at DojoLive, thank you guy for joining us today, than you to our audience they’re always loyal to us and they see every DojoLive that we broadcast, thank you so much and see you next time.

Carlos: See you next time, thank you everyone.