The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 2 months ago

185: The Key Is Personalization at Scale

ABOUT THIS EPISODE

In this episode of the Sales Hacker Podcast, we have Appy Choudhary, Head of Sales Development at Blend, where he has built and leads AE and SDR teams as a sales leader with nearly 15 years of experience. Join us for an authentic conversation about applying sales leadership to building SDR teams — and the role of personalization in generating opportunities.

What You’ll Learn

  1. Personalization makes a difference in prospect response
  2. Video mail and messaging is a huge personalization aid
  3. The SDR role is all about learning and being coachable
  4. Hiring people early to tech sales is ultra rewarding

Show Agenda and Timestamps

  1. About Appy Choudhary & Blend [1:50]
  2. A sales leader’s hiring process [6:02]
  3. Using personalization and creativity to drive responses [9:05]
  4. The unexpected in sales leadership [13:30]
  5. Advice about generating opportunities [19:30]
  6. Paying it forward [20:53]
  7. Sam’s Corner [22:17]

One, two, one three,hey everybody, welcome to the Sales Acer podcast. It's your host, SamJacobs. Today in the show we're talking sales development and pipeline creation with appyChowdrey. It's a great conversation and I'm really excited to bring it to you. Before we get there, we've got three sponsors. The first is outreach, a longtime sponsor the show. We're excited to announce unleash summit series isback. This year's theme is the rise of revenue innovators. Join the newcohort of leaders who put buyers at the center of their sales strategies to driveefficient, predictable growth across the entire revenue cycle. Get more details and saveyour spot at summit. That outreach I owe whilst are sponsored by pavilion.Pavilion is the key to getting more out of your career. Our private membershipgives you access to thousands of like minded peers, dozens of courses in schoolsthrough Pavilion University and over Onezero workbooks, template scripts and playbooks to accelerate yourdevelopment. Pavilion members get hired twenty two percent more quickly and paid fourteen percentmore, and are promoted thirty percent thirty four percent more rapidly than their peers, based on study recently conducted. Unlock the career of your dreams by applyingtoday at Joint PAVILIONCOM. And finally, Conga, a new sponsor on theshow. As doing business becomes increasingly complex, it gets harder to do it well. Business is often sacrifice agility and loose sight of the customers experience.CONGA's expertise and comprehensive solution suite for commercial operations, transforming the documents and processaround and customer engagement. CPQ AND CLM help businesses meet customer needs while increasingagility to adapt to change. Check them out. CONGOCOM forward slash salesactor.Now let's listen my conversation with Appy Chaudry. Hey, everybody, it's Sam Jacobs. Welcome to the salesaccer podcast. Today in the show we're excited tohave appy choudry. Appy is a sales leader who has over fourteen years ofexperience with an MBA and engineering background. He is built and led a eAndsdr sales teams, achieved individual revenue quotas, developed go to market strategies, managedregional sales and recently has been a hiring machine. He's hired thirty fivereps in the last three years. Appy, as a top performer at his currentcompany, blend, built an strm as Dr Team from scratch at hisprevious company, launched darkly, and has also been a director of sales.He's well versed in different sales methodologies, including sailor medic, and has gonethrough various sales leadership trainings such as Sassy with my friend Matt Cameron, tenpound and closed loop. Appy, welcome to the show. Hi Sam,thanks for the warm welcome. We're excited to have you so here the headof sales development at blend, and we're going to dive into your experience atlaunched darkly, but first we want to understand a little bit more about blend. So what is blend? Blend is a digital lending platform that helps banksand credit unions go through the mortgage lending process smoother and faster. Oh,I love it. Awesome. How big is the company? Roughly from youknow, and you can tell us number of employees or they are are,however you want to frame it. We just acquired the early big company calledtitle. Three hundred and sixty five and after the acquisition we're a company withalmost two thousand and three hundred employees. Oh Wow, amazing. And you'rethe head of sales, of elopment for for that entire organization. Yes,exactly. Well done, sir. How how big is your current team?My current team is the team of fifteen st years, including team leads,managers. And Yeah, we've we've grown the team quite a lot. Infact, most of the team is relatively new because we've been promoting hiring.There's a lot of attrition, good positive attition on the team, as thisteam is also the junior talent pool for our sales organization. So that's prettyexciting. That is exciting. So let's let's first just understand. You know, how you got here. I read in your by you've got fourteen yearsof experience. You've got an engineering background and MBA. But how did youget into sales in the first place? How did you find your way fromengineering in a sales tell us at a bit about your wife, your wifestory in terms of education, I started off as an engineer and then slowlygot into sales engineering, supporting and consulting...

...techy clients, and that's where Irealize that I'm much better off in sales rather than engineering. I started traveling, meeting clients, traveling to go to conferences, and that's what got meinto sales and since then I've been focused on selling business and closing revenue targets, leading sales people. And here I am so appy. You know,you mentioned that you're one of the founding members of this company, launched darkway. Talk to us a little bit about that experience and about building thattheme, because I know it's pretty formative for you. Yeah, it wasan interesting and exciting time. So I was hired by our VP sales,hector hernand is, back in the day and Hector hired me to build thestr function from scratch. It was a series B company with twenty five tothirty employees and I was basically the fourth sales member on the team. Ijoined them, built the initiated the str playbook. After three months, whenwe started getting some outbound and inbound results, I started hiring strs, continue torevamp the playbook understand what kind of folks we should be hiring and withina span of two years a lot happened. I hired and onboarded over twenty fourstars. As a direct hiring manager, I led three SDR leaders on myteam, promoted eight strs within different departments of the company, including sales, enable men, sales operations, account executive CSM roles. I myself gotpromoted SIS my manager change thrice and on boarded some really cool tools such asoutread zoom in for Polo exc overall, it was a pretty exciting time whereI got to work for an awesome product with truly amazing and smart people.What did you learn about hiring? You know you've hired a ton of peopleat this point. As about your hiring process, your methodology, how yourun the end of your process? Walk through walk us through it. Yeah, so, talking about the interview process, it's basically I do the initial phonescreens. It's there, usually for an hour, and then, ifthey go well, I usually send candidates in assignment, a simple assignment tocheck out their writing sample and then invite them for an onsite, which isnow virtual, where they meet myself and a couple of leaders in strs onmy team and go ahead and extend and offer. Talking about my methodology onhiring, I look for five to six most important skills in this role.That include someone who's coach, a bill, because this role is all about learningand growing. It's a stepping stone for anyone. Someone who's organized,because as an STA, you're dealing with thousands of leads, slack, differentGoogle sets, sales force reports, excel files, etc. So you reallyneed to be organized so that you can keep up with your tasks. Someonewho's self motivated and hard working, as you'll receive a lot of rejection inthis role. Ninety nine percent of your efforts are going to get a resultof no, I'm not interested, so you need to be super self motivatedand have great persistence around your work. Someone who, in general, iscurious, because if you're curious, you'll probably really want to know what problemschallenges your prospects are facing. And then, finally, someone who's creative, asif you're creative, you can think about creative messaging, think about differentways of outreach and connecting with your prospects. So these are the five to sixthings I look in candidates when I am interviewing them. Let me askyou about wfore. I have a couple...

...of questions, because you are selvesdeveloped an expert. First, how long do you think somebody should be anstr before they're promoted to account executive. Twelve months on the lowest end andeighteen months to is basically the Max Garana and and because I'm you know,Trishper Tu Day has commented in the past that there's some data that if you'repromoted before twelve months, oftentimes you're fair. Your Rad as account executive could bevery high. Yes, exactly. That makes total sense and also dependson what kind of company what market you're selling in. Example, at blendwe mostly sell to enterprise financial organizations and selling the sale cycles are really long. A lot of MSA's red lines and contracts, so you need a lotof experience are selling to those kind of accounts and that's why usually you needto be an Stt for eighteen months, as the learning curve is a goodone. But in general twelve months is the least I would recommend, becauseI'm sure you know, outreach and seals, loft and all these tools are theirblessing and a curse. They enable people to send lots and lots ofemails all at once, but the issue is that buyers are becoming inundated andunresponsive to these messages. And it's becoming harder and harder to get somebody's attentionin the thoughtful way, in a way that enables them to want to leanan engage and perhaps become an opportunity to your company. So what do youteach and what do you do and what creative strategies are using today in orderto drive positive responses from from your prospects? So very well said, Sam otherthan just sending those regular emails and making those random phone calls, thereare a lot of things my team does in reaching out to these prospects.That include we have a a really good gifting strategy, so we use sendThoseo as a tool to send personalized gifts and experiences who are prospects, tograb their attention and have a conversation with them. We use a video outreach. We've used cameo in the past, so my reps, they go ontwitter, research prospects, find out who their prospects follow, what do theylike, and then find their celebrities on cameo and have them send certain videos. That gets US quite a bit of traction. And then including different socialselling strategies, including sending voice notes on Linkedin, sending a selfie video onLinkedin, using jifts in their emails. So all of these creative strategies maketheir emails stand out, make their call stand out and help them be successfulin their current role. The question is, the feedback you might get from awrap is happy. Listen. I hear you, man. I wantto send a personalized video, I want to do a selfie thing, Iwant to go on cameo and do some research on twitter, but my prospectwas just too big and I just don't have the time, given the targetsthat you're giving me in terms of twelve to fifteen qualified opportunities every month,to to do all of that prep work. What would you what is your responseto that? It basically needs to be a balance of your outreat Iask them, I don't want you do all of this for your entire prospectlist, but I'm not even asking you to not do all of this andjust mass blast your prospect list. I help them in prioritization, in breakingtheir prospect list into different tiers, in segments, let's say, example,tiered one, are the biggest, most important accounts they need to break into. So selecting the top decision makers at each of these accounts and then focusingon them, doing the most personalized outreach...

...to this tear of bunch of people. And then it's the second badge with medium kind of personal medium level ofpersonalization, and the third tier is basically where they can use the least amountof personalization and more automation. That makes a lot of sense and I've heardthat from some other folks. So if you're talking about Tier A, right, you're very top most important accounts. You know, typically you know acold call. You know cold call to opportunity creation, or maybe it's liketotal could call the win rate is like one person or two percent. Butwhat do you what should the percentage be? If, for your tier a accounts, of your ability to create an opportunity, if you selected them reallywell and you've done this love of personalization, how many of those accounts should yoube able to at least create an opportunity from? It's usually, Imean it depends on quarter to quarter and I'm sure you understand that, butit's usually five to eight or sent where my reps are able to generate opportunitieswithin these tiered one accounts, where they invest a lot of time and personalization, create specific sequences on outreads and do a ton of research. They alsowork with their account executives and build build or charts, understanding and finding what'sthe buying committee? How do they look like in doing specific outreach accordingly?I like that. So you heard it here, folks. Five day percentthose you know. So you're in your current role. What's your I guesswalkers through your journey from an individual contributor to a leader and what has struckyou as the biggest thing that was sort of unexpected? What did you notexpect about being a leader? That is definitely a part of a job thatyou weren't you aren't quite expecting doesn't mean you weren't ready for it. Doesn'tmean you're doing a bad job, just means you aren't quite expecting it.So I started off as an individual contributor, as an start initially, and thengot into an account executive role where I was closing business by myself,and sales back in the day, before eight to ten years was very differentthen compared to doing sales now. And after being in that individual contributor rolefor four and a half years, I got into a director of sales rolewhere I was managing account executives who were responsible for closing business. I didthat for three and a half years and I thought that was the most excitingpart back then. And then after that I moved into specific str leadership.I wasn't expecting that this role is going to be so challenging but at thesame time it would be so rewarding and so motivating personally. And the reasonI say that is in this role I get an opportunity to hire super talentedyoung people, maybe fresh out of college or their first or second job veryearly, to take sales. So I get an opportunity to hire them,train them and set them up for success for their entire career. I've oftentimesseen where few of my strs who were strs before five to seven years,they reach out to me after five to seven years sharing how successful they areand they are still using some methodologies or some part of the playbook I createdfor them, and that is pretty pretty satisfying. It's exciting and motivating thatI had such a big role in their entire sales journey, in their entirecareer, and I was not expecting this when I got into str leadership,but that's what I love about this role. And then the second piece of itis I wasn't expecting this to be...

...so challenging and at the same time, there's so much to learn and grow from every individual. It's very differentwhen you hire an account executive who has three to five years of closing experiencecompared to you hire someone who's fleshed out of college or when it's their firsttakes his job. You need to spend a lot more time with a freshcollege graduate. You need to teach them how to behave in meetings, youneed to understand their thought process, you need to get there by and youneed to explain them small things. So there's a lot of time, investment, cleaning, enablement that goes into leading str teams and I wasn't aware aboutthis when I was taking this challenge, but I've definitely grown into it.What a what are your plans for yourself? You know you're running an str teamnow and a company that's now, I think you said, twenty threehundred people. Where do you want your career to go? And you know, one of the challenges people sometimes comment about us to our leadership is thatif you move directly from str I see it if it's a contributor to us, to your leadership. You don't get the account executive closing experience and sothe str manager position cannot be as clearly defined as part of your career progressionas being like a sales manager for account executives. How are you managing thatchallenge if it isn't even a challenge? You may disagree that it is achallenge, and what are your plans for yourself? You know, where doyou see your career going over the next couple of years? So I definitelyagree to your statement around it being a challenge. In an ideal world,I think a str should move into a closing account executive role, gain thatexperience and then try to get into specific management, maybe starting from the STRteam or directly getting into a SMB or midmarket account executive management role. Icertainly agree to that, because that's when you because from an STR's perspective,the account executive is the strs customer and you need to be in the customerspot to understand what do you need from an str or an str manager.So I highly recommend folks to get into an account executive role, gaining experiencein that role before getting into management. Now the second part of your question, my career plans. It's interesting to see how str leadership has become soimportant and is becoming more important in the recent three to five years. Iremember when I first met David Delany from ten bound. He shared with mebefore three to four years that happy. At this point of time I don'tsee a lot of str managers, SDR leaders. A lot of companies lookingfor str leaders, but within a span of the next three to five yearsyou'll see often that companies need a weepy level of executive to run this team. And here we are. I see a ton of peers who are inthe space as vpcs development. I get a ton of recruiter outreach for thosekind of roles and my plans is basically to continue to grow within this rimand lead different kind as to our teams. Manage frontline managers, manage director ofsales development and take it ahead. I love it. Couple ask questionsbefore we go happy. We talked about this a little bit earlier and youmentioned a couple really creative strategies for your tier accounts. But let's say I'ma I'm an str manager, I'm hiring five Reps. I'm under, youknow, under a Truantou amount of pressure to help my company grow and createpipeline. What's your piece of advice? And we can give a high levelpiece of advice, but also give us like your favorite contactic in terms of, you know, generating opportunities and creating awareness for the company. My adviceto them would be to spend some time...

...of their day thinking about how tosolve challenges each individual rep is facing on their team and how can they bereally effective in removing those blockers and challenges and if they if they don't knowhow to do that, then definitely going ahead and connecting with their leader sothat they can well equip them. They can train them or they can outsourcethat training for them so that they are able to solve those challenges. Oncedone, I'm sure their St Gus would be successful in their role, theywould be able to hit their Kuta, they would be able to grow anddevelop themselves and that would also set the str manager up for success. Ilove it. Happy. Last question we have for you is really sort oflike a pay for question. A lot of people have influenced you. Youhave a lot of mentors, you have a lot of founders. You havea lot of people that you are aware of that have helped get you werewhere you want to go. Who are some people that you think we shouldknow about? My weep of sales from launch darkly, who's now at traceabledought AI, has had a big role in my career journey, specially inthe last three to five years. He's helped me grow learn, he explainedme the importance of processes, documentation, hiding the right people and supported meand all of that. I also follow a lot of stas and sales leaders, including Sam Nelson, Beg Holland, Jeremy Donovan and Mark Coast of Globe. Awesome, happy folks for us in the rest and I'm sure they're goingto have some some questions for you and maybe want to pick your brain ormaybe how you as a consultant, if you're hopefully allowed to do that withyour current employer at blend. What's the best were to get in touch withyou? Linkedin is the best way to get in touch with me. I'mpretty active on Linkedin, so feel free to connect me correct with me onLinkedin. Awesome, happy thanks so much for joining us on the Selvesycer podcasttoday. Thank you. Some wonderful chat things again, everybody Sam's corner reallyenjoyed that conversation with Apach Odre. He's clearly a student of the game andwhat's what's? You know, he has studied. So what does he learned? He's learned that personalization is the key. I know companies that read predictable revenueten years ago and they are convinced that that is the way to dothings forever and ever and ever and playing text emails saying who's the right person, or my are you the right person, or those emails where it's like,I see you have been responded and it's like the seventh email and athread y'all that stuff doesn't work anymore. It doesn't work and it shows thatyou're not very thoughtful or creative. So you don't want to look like that. You want to look thoughtful and creative. You got a personalize. You haveto personalize. personalization at scale, well, I don't know what thatmeans, but you got a personalize. At these teams use video, theyuse Sendoso to send people things in the mail. They use text messaging,they use linkedin voice memos, they learn, they use linkedin selfie videos, theyuse platforms like bombomb or videyard to a chord videos of themselves. Theypersonal apting mentioned in the show that he uses cameo. So the reps havea budget. They go to your linkedin or twitter profile or facebook page orwhatever. They figure out. If you're a buyer, what are the thingsthat you really like? For me it's, you know, the Washington football team, unfortunately, Washington capitals. Maybe some real housewives, but only ofBeverly Hills and they'll go out and they'll get not to read. Never torate. I don't like to rate, but I do like Kyle. Ido like Kyle Richard. She's a good person, married a long time.Love Mauricio. He's an entrepreneur agency, I think is one of the largestreal estate agencies in La. So here's...

...the point. If Kyle, ifI ever got a cameo video with Kyle tyl talking to me about pavilion,I probably respond favorably, or at least Evander Pop Lbpol, but she's notgoing to show anymore. Maybe Tom Sandoval or Tom Schwartz from vander pump rolls. Have you seen sander vals like mustache and facial constructions, weird stuff,but I dig him. Tom Tom's a reasonably good bar. That's not thepoint. The finest personalization of my friends personalization. You're going to have tofind a way to do it. It was just on a conversation with acandidate to work with me at pavilion and you know what did I say?I said bring your brain. Bring your brain. You got to show upwith your brain every day to work. Don't read from the script. Wedon't need robots. If you're going to be a robot and just be robotic, I'll just hire a robot. I don't need a human being with upand down energy and emotions and moods and all that stuff, if you're notgoing to bring the creativity, the ingenuity, the passion, the authenticity that humansalso bring. That's why we tolerate the inconsistency, because you're a humanbeing. So if you're just going to be a robot, pressing but pressent, go on an outreach sequence and blasting you with stupid emails, go home, pal go home, get out of here. But we don't need it. We're not buying it, but I am buying it's personalization, thoughtful outreach, research and just a general sense of compassionate empathy and curiosity from the peoplethat reach out to me. All Right, I'm done. If you want toreach out to me, Ken Sam a joint PAVILIONCOM. If you wantto thank our sponsors, we have three outreach transforming the productivity of sales peoplethe world over. A check out there unleash summit series. Summit that outreachOteo Pavilion, the company that I work for. Pavilion members get hired twentytwo percent more quickly, paid fourteen percent more and promoted thirty four percent moreoften than their peers. So check them out unlock the career of your dreams. That joined pivilioncom and Conga really incredible company. They combine customer needs withincreasingly agility across customer and engagement, CPQ and CLM, customer life cycle management. To check them out at CONGOCOM forward slash sales hacker. Otherwise, giveus five stars on itunes. I said something that upsets you. Don't giveus any rating at all. Just be quiet. It's fine. Go dosomething else today, but if you really like what I said, if you'refan of Maurracio or kyle or you don't like to rate, give us fivestars on itunes. Otherwise, my friends, I will talk to you next time.

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