By Matt Heinz, President of Heinz Marketing

Another episode of Sales Pipeline Radio for you!  Catch us LIVE every Thursday at 11:30 a.m. Pacific.  It’s just 30 minutes long, fast-paced and full of actionable advice, best practices and more for B2B sales & marketing professionals.

We cover a wide range of topics, with a focus on sales development and inside sales priorities heading into and throughout the year. We’ll publish similar highlights here for upcoming episodes.  You can listen to full recordings of past shows at SalesPipelineRadio.com and subscribe on iTunes.

We were thrilled this last time to be able to talk to Samuel Sunderaraj, VP of Sales at Skilljar.

Samuel will answer some great questions:

What’s the state of SAS sales?

What does it look like today? And for folks that are either at the front lines or managing an SAS organization, what are the keys to making SAS sales work today?

He’ll also talk about how good sellers can actually be still at the forefront of the buying process, at the top of the buying process to provide that value.

He’ll share about the people side of growing a sales organization. It’s one thing to put numbers in a spreadsheet and say, “Well, if we call this many people, convert this many deals, we’ll hit our number,” but you still have people that you’re managing as part of that.

Hear about the importance and some of the keys to building a sales organization, a high performing sales organization that also prioritizes the people within it.

What about managing expectations? What about the boards objectives? What about the investor objectives? How do you manage that when you’re in the middle and you’re leading the sales organization, having to motivate the team, but also sort of set expectations from above?

All this and a lot more!

MORE ABOUT OUR GUEST:  

Samuel Sunderaraj has the following experience in sales management:

Driving and initiating contact with senior decision-makers at Small To Enterprise Accounts (C-level)
Scaling revenue from $0m to $30Million+ in ARR
Revenue retention ($30M+)
Building sales teams from 1 to 30+
Experience in building a successful sales organization from scratch, including recruiting, hiring, and developing compensation plans.
Leading sales teams that are metrics driven & efficient
Start-up advisor

– Building high performance sales teams that are metrics focused and scaling for growth
– Focus on customer & company success (“customers pay the bills”)
– Sales metrics execution – managing cost of opportunity acquisition while driving top line revenue
– Territory and Market Optimization – executing to high conversions on the active funnel.
– Creating Value = sales multiple
– BOD Metrics & Analysis
– Funding (Seed, Series A-C,)

Learn more at Skilljar.com

Matt:  Thank you everyone for joining us on another episode of Sales Pipeline Radio. We are here every Thursday at 11:30 Pacific/2:30 Eastern live. SalesPipelineRadio.com. Past, present, future episodes. You can check them all out. You can download them on demand. Every week we’re featuring some of the best and brightest minds in B2B sales and marketing. Today is no different. Really excited to have a good friend, long time sales and marketing and go to marketing executive, Samuel Sunderarajj. He is the VP of Sales at Skilljar and we had a last minute cancellation. You were so good to join us kind of last minute. So we really appreciate you moving your schedule and, Sam, thanks very much for joining us today.

Samuel Sunderaraj:  Yeah. Thanks, Matt. Thanks for having me. Like I said earlier on, you’ve definitely upgraded. So I am an upgrade, right?

Matt:  This is absolutely an upgrade. Are you kidding me? I wanted to have you on for a while and this just worked out really, really well. You have been in deep in B2B sales throughout the west coast, in the valley, up here in Seattle for a long time. Heading up sales of companies like Simply Measured, Extra Hop, LiveStories, and now recently joined the team at Skilljar, which continues. I think your customer base grows by two X it seems like every month these days. So doing some great stuff there. But maybe just kind of start with just talk about what do you consider, if I were to say what’s the state of SaaS sales? I mean, you’ve been doing SaaS sales for a while. Where are we at? What does it look like today and for folks that are either at the front lines or managing a SaaS organization, what are the keys to making SaaS sales work today?

Samuel Sunderaraj:  Yeah. Great question. So when I started off in SaaS sales back in the day, the buyer pretty much depended on the seller for information, right? I’m talking the days of 2001, 2002. This is when Salesforce came to the market and started being the kind of up and running SaaS CRM play. Then you fast forward to 2004, 2005, it was very much kind of the hey, I’m going to get on the website, sign up on the lead forum, somebody call me up, and went through a discovery process, and then we setup a demo. But the buyer still was primarily educated for the seller, right? Today with the buyer journey and there’s a couple things happening.

Once is, and I’ve always said this, kind of saw this start back in 2011. We started to see the trend where buyers became more informed before they even picked up the phone and called the seller, right? So that’s primarily what’s changed, right? The buyer has more access and knowledge. At times we’ve even seen buyers that are ready to buy without even having a conversation with a salesperson, right? So they’ve gone online. They’ve engaged with content. They’ve seen blogs, and organizations like HubSpot did a phenomenal job in terms of building content and kind of turning that machine into a very buyer centric approach, right?

So if you ask me what’s changed, I would say the integrated approach to marketing, the content being delivered to buyers in real time. That’s probably changed the game. When that phone rings or when that buyer raises their hand, seller better align to what the buyer’s learned about your solution. So that’s been a tremendous change. Yeah.

Matt:  Certainly is changed the buyer being more educated, the buyer being more self-directed. I don’t think that necessarily changes the opportunity for sellers to provide value, right? I mean, I think sellers maybe historically have come in and been in the source of education. Think the bars a little higher, but talk about how good sellers can actually be still at the forefront of the buying process, at the top of the buying process to provide that value.

Samuel Sunderaraj:  Yeah. Exactly. No, great question. Again, so the other piece of this is also as a seller you should be educated about the buyer, right? So one of the things that you need to have or understand is what is the objective, what is the business objective, what is the growth objectives that you’re looking to address or looking to align when it comes to the buyer. So gone are the days of feature functionality, obviously have a great product to sell, but more important, it’s getting to know the buyer, right? What does the buyer need? How does the solution map to what the buyer is ultimately going to solve?

Having done this myself, when I was carrying the quota back in the day, the assumption is this comes down to relationship, which is partly true. But at the end of the day, people buy business applications, SaaS because it solves a business problem within their business. They’re looking to buy because it’s going to move the needle for their respected businesses. So that’s the key for a seller really to understand what is it I’m selling, what is the impact of the solution that I’m selling to the buyer’s organization, and really making sure that every interaction whether it’s the demo, the discovery, the follow-up, the proposal review aligns back to the growth objectives of the buyer.

Matt:  Talking to Samuel Sunderarajj today. He’s the VP of Sales at Skilljar and has spent last several years managing and growing sales organizations. I’m struck by the headline on your LinkedIn profile, Samuel. It says, “Building teams and scaling revenue.” Talk a little bit about the people side of growing a sales organization. It’s one thing to put numbers in a spreadsheet and say, “Well, if we call this many people, convert this many deals, we’ll hit our number,” but you still have people that you’re managing as part of that. Talk about the importance and some of the keys to building a sales organization, a high performing sales organization that also prioritizing the people within it.

Samuel Sunderaraj:  Yeah. No, absolutely. When we talk about buyer empathy, we also need to talk about seller empathy and by this I mean how do you get high performing teams or how do you put together or bring together a diverse set of individuals to perform at a high level, right? So my famous … I’m a big fan of coaches, as you know, and one of the reasons, one of the key reasons I follow and followed Belichick for a long time, Bill Belichick, the coach for the Patriots, is because he’s such a systems player. He brings in different players from different backgrounds, different systems, puts them together, and gets the best out of them.

So one of the things I’ve learned as I’ve grown in my career from sales manager to sales director and VP is ultimately at the end of the day, you could build a process, you could write down a process, you could whiteboard a process, but this comes down to people, right? In terms of how do you get people to perform at a high level, it’s the buy in. The buy in to the process, the buy in to the system, sales process, execution, being data driven, and ultimately understanding what is it that motivates them.

Samuel Sunderaraj:  We’ve got a pretty diverse team and in my background and past experiences and in my current experience or role, these are individuals with varying degrees of experience. How do you bring them together and make them understand that these are expectations, this is the data, but also get them to understand that this is a buy directional relationship, right? So this is not just your number or your process. This is my number as much as it is their number. So for me that’s the fundamental … Then yeah, sales process, methodology, prospecting, self-generating a pipeline versus being a completely dependent on the ADR or SDR organization, right? All of these, what I call different plays, you got to bring them together and make them understand what’s the playbook look like. Then there’s a lot of testing, coaching, reinforcement, and then there’s a lot of re-architecting the system as we were saying.

Ultimately, it’s people, right? So understanding psychology, understanding what motivates them, and I’m a big believer in roadmaps, right? So every one of my team or folks that have been on my teams, I get into this roadmap exercise about where do they want to be, what motivates them, right? Then kind of working together to make sure that we’re able to help them accomplish that.

Matt:  Just a couple more minutes before we got to take a quick commercial break here. But just follow along question, how does that change or how do you have to adjust your approach for different generations of sales reps? You’ve got many sales organizations inside sales teams especially have three to four different generations of professionals. Are you making adjustments to that approach based on millennials versus gen X versus Boomers?

Samuel Sunderaraj:  Yeah. Absolutely. That’s a great question. I think a few years ago I would’ve said no, it’s one size fits all. It’s a template. Off you go. I think these days it’s about understanding for some people millennials, as you said, it’s about having a seat at the table. It’s about having influence. It’s about coming across as leaders or being leaders, right? So you don’t have to have a team to be a leader. So one of the things that I note down or at least specify on my one on ones is leadership qualities, right? So if you have ideas, you have tactics, you have something to share, let’s collaborate. Let’s share with the team, and if it makes sense, let’s implement. Let’s execute. I think that saves a lot. So for a lot of millennials, they want to have a seat at the table, right? It’s a little bit misunderstood, but I think when you sit down and talk to them and understand where they want to go and what they want to do and how they want to fit into the sales systems, I think it comes down to having a voice, having a true seat at the table.

Matt:  Awesome. We’ll be right back. We’ve got a lot more with Samuel Sunderarajj, he’s the VP of Sales at Skilljar. We’re going to be talking about the sales and marketing relationship. We’re going to talk about how to set expectations with leadership and boards and investors that sometimes have different accelerated ideas of what could happen in a market. Balancing all of that, a key part of the job for heads of sales and SaaS startup companies. We’ll talk a little bit more about that. We’ll be back just a couple minutes here on Sales Pipeline Radio.

*Break*

Matt:  That’s right. Absolutely. Thank you very much, Paul. Thank you very much again for joining us. Sales Pipeline Radio. We’ve got more with Samuel here. We’re going to talk more about SaaS sales and expectations. Make sure you join us every Thursday at 11:30 Pacific/2:30 Eastern next couple weeks. The last day of May, next Thursday, we’ve got Dave Gerhardt. He’s the VP of Marketing at Drift. If you’re not familiar with Drift, they’re trying to eliminate the landing page and make it easier for prospects, buyers, and sellers to connect by getting beyond the landing page, registration page where you have to sing. After that, we also have Patrick Morrissey, he is the CMO of Altify. Another fast growing SaaS startup. Similar conversations, quite frankly, what we’re talking about today with Samuel but on the marketing side, how to manage that growth.

Back to our guest today, Samuel Sunderarajj. He’s the VP of Sales at Skilljar. Let’s talk about managing expectations, Samuel. But let’s talk about the other side. We’ve been talking about managing teams, motivating teams, making their objectives your objectives. What about the boards objectives? What about the investor objectives? You’ve worked multiple times in companies that are VC backed. They’re investor backed. Where investors clearly want their money back and want to make some multiples on their investment. Sometimes the speed and the maturity of the market does not match expectations or at least hopes. How do you manage that when you’re in the middle and you’re leading the sales organization, having to motivate the team, but also sort of set expectations from above?

Samuel Sunderaraj:       Yeah. No, I think that’s a great question, especially for any sales leader that’s leading sales in a venture backed environment. I think one of the things that I try to do early on is to get a pulse of the board, right? You can understand a lot. You can get a lot when you know who the board members are and what they’ve done in previous investments. Now I’m fortunate to work with a board that comes with a lot of experience and some great exits. Two of my board members actually were one of the first investors in Marketo, an organization that you’re very familiar with. The thing about that is are they there to help you figure it out or are they there to just talk about the numbers, right?

One of the things that is important to set expectations with the board and a lot of experienced board members have seen successful exits. They’ve seen the playbook and they’ve seen what worked. How did the machine happen, right? When you talk about sales and market and go to market, the expectations as far as the board goes is obviously you want to be realistic with the numbers, right? Board members want transparency, right? They want to know if this is a sales leader that has a path to get there, right? If you’re behind in the hiring plan, be up front about it. How do we fix it? If you’re behind on numbers, you want to help them understand what is the analysis say and what are you looking to fix. If you’re trying to fix that issue, does it help with predictability? At the end of the day, this is all about building a predictable business, right? The great businesses and the great outcomes happen when you’re able to build a predictable business quickly, right? So eventually you want to get there.

So I think board members and boards, it’s exactly that, right? Is the sales leader aligned with them when it comes to the outcome? The outcomes not going to happen in two months or two years, right? A lot of the recent IPOs that we’ve seen from DocuSign and SmartSheet, I mean, these are startups that were founded in 2003. So it takes them a while to figure it out. It’s a marathon, not a sprint. But in terms of working with boards, it’s expectations, it’s transparency, it’s alignment on what is the model say and is there a path to get there? Is it market execution, is it sales execution? When you don’t hit the numbers, getting ahead of it, right? That’s key. If you’re not going to hit the plan, make sure you get ahead of it and communicate it, and come up with a strategy to fix it. That’s how I tend to work with boards.

Matt:  Got a few more minutes here with Samuel Sunderarajj. He’s the VP of Sales at Skilljar. I want to ask a simple question that may not have simple answer. Let’s talk about managing expectations, Samuel. But let’s talk about the other side. We’ve been talking about managing teams, motivating teams, making their objectives your objectives. What about the boards objectives? What about the investor objectives? You’ve worked multiple times in companies that are VC backed. They’re investor backed. Where investors clearly want their money back and want to make some multiples on their investment. Sometimes the speed and the maturity of the market does not match expectations or at least hopes. How do you manage that when you’re in the middle and you’re leading the sales organization, having to motivate the team, but also sort of set expectations from above?

Samuel Sunderaraj:  Yeah. So when marketing number one, I want to be completely aligned and I like the fact that some of the more contemporary market leaders or at least what I’ve seen and read and heard are thinking about how does marketing be assigned a revenue number or marketing’s bonus is paid on the revenue number, right? So I like that. First off, it’s a shared responsibility, right? So if they’re bought into that, may not be 100% because I understand some of it is out of their control, especially when we talk about salespeople who have taken the SCOs and running with it, I get it. But fundamentally for me I’m looking for the market leader, the marketing teams to sit down with me and understand what’s going on with the funnel, what’s the pulse of the funnel, right? Top down, from net new, MQLs, SQLs, or SQOs, right? I want to make sure that when it comes to targeting the ideal customer profile, we’re on the same page.

It’s not just about marketing racing to a number, right? Let’s talk about how is marketing getting to the number and let’s talk about the pipeline, right? Then let’s talk about close one business. So I think synchronizing throughout the funnel is important, right? In the old days and even in some cases today, you see marketing high fiving. They’ve hit the MGL number. They’ve hit the SQL number, and then you look over on the sales side and the mood is not quite excited, right? The mood is still damp because here we are trying to get deals across the finish line or there’s something wrong.

But I want the market leader to be side by side with a sales leader to really understand what’s going on throughout the funnel, not just up.

Matt:  Absolutely. Yeah. I think what is that require in organizations that maybe want to do that strategically but need to convert that into operational alignment? What do are the keys to getting a marketing organization, for instance, that maybe is used to just most leads at lowest possible cost to now start thinking about pipeline contributions, marketing influence on closed deals, more quality versus quantity. I know you’ve seen this migration, some successful, some not in a lot of organizations. What are the keys that make I a little more successful?

Samuel Sunderaraj:  Yeah, I think they key is really alignment throughout the funnel, throughout the team, right? So when I say alignment, okay, let’s establish an SLA. Okay. Here are the numbers. Now SLA should not be long. I think here are the numbers. Okay. Here is the number the marketing signed up for. Here’s the weekly production. Don’t be ambushed at the end of the month, right? With 500 MQLs in the last few days of the month. We know what the intent there is. So I’m talking about VP forecast. Where the marketing leader and the sales leader are sitting down side by side and saying okay, here’s what’s coming. Here’s the plan to touch these leads, and here’s the sequence and here’s the activity sets assigned in terms of how we’re going to prosecute those leads. Here are the conversion number that the ADR, SDR organization can sign off to. Whether it’s organic content, organic leads, and then obviously there’s an outbound component to that market can help.

So again, it’s signing up for a number, it’s tracking conversions throughout the funnel, and then whether it’s a good week or a bad week, try to understand okay, what’s working, what’s not working, and if something working, both are in agreement to make sure that we repeat that again. So there’s this constant alignment as I call it or continuous alignment where it’s we go a week synchronizing and touching base and meeting about what’s happening, and then the other thing, right? ABM. Right? Big part of outbound. How does marketing enable ABM, account based marketing, or I call it account based prospecting. Marketing is a key component there because you’re going to help us build landing pages. It’s not that cold call is dead. It’s just that we want to be the messaging and the calling and the voicemails that we need are relevant to the buyer, right? So building landing pages, right? How does marketing help?

Samuel Sunderaraj:  So this is obviously a combination of implementing an SLA, it’s a combination of having those meetings in your calendar, and then it’s a combination of looking at the spreadsheet, working with sales ops and marketing ops to ensure that the conversions are tracking. If we’re behind, what are the behaviors we change on both sides?

Matt:  Wrapping up here with Samuel Sunderarajj, the VP of Sales at Skilljar. Before we have to let you go and ask you a question that we ask a lot of our guests, especially those on the sales side. If there was a Mount Rushmore of sales, Samuel, if you could think about the people that have had an influence on you in your sales career, they can be dead or alive, they can managers, they can authors. Who are the people that have had the most influence on you in your career that you might recommend that people seek out as well?

Samuel Sunderaraj:  Yeah. I think the one having being out there the early days of Salesforce and just having competed against Salesforce being a CRM salesperson, on premise CRM salesperson, enterprise as we called it back in the day. Got to see how Marc Benioff executed on the initial phase of Salesforce. Right? Lot of them had deals 10 seats, five seats, six seats. I lost a few deals to him and his team back in the day. So I would put Marc Benioff. I would definitely out there or on one of those mountains.

The second person definitely Manny Medina, the CEO of Outreach. Again, similar type except I’m a little closer to Manny. I know Manny, and just seeing somebody pivot from literally going on a business, staring at the barrel of a gun, if you want to put it that way to really hustling, making it. Manny’s a fundamentally just muscled his way through selling a vision into what is now a half a billion dollar organization in a span of four years. Completely go to market execution there.

Third is somebody folks may not know, but a guy named Jeff Althouse who was I as in ADR to Jeff many years ago. He was a sales rep that brought in three, four million dollar deals on a quarterly basis consistently when I worked at Pivotal Software in Canada. I learned a lot as an ADR, Jeff would actually have me on the phone with clients during negotiation calls. I just got to see him close massive amounts of businesses with buyers and that was fascinating to just follow him and watch.

So those are kind of the three folks I’d put out there.

Matt:  Good insights for sure. Thank you so much for our guest today, Samuel Sunderarajj. He’s the VP of Sales at Skilljar. Appreciate him joining us last minute. This was absolutely an upgrade. It’s hard to know if he was an upgrade because we don’t know what the previous guest would have brought, but honestly this was a great conversation from someone who is still in the trenches leading sales organizations, still has a number to hit, and I know you’ve got a month, a week left in the month. Even though you’re new at Skilljar, you’ve got to hit that number. So we’re going to let you go. Thanks again to our guests today.

Join us every week on Sales Pipeline Radio. We’re going to have a bunch of great guests coming up next week. Dave Gerhardt, he’s the VP of Marketing at Drift. If you want to get rid of your landing page or wondering how the heck you could live without landing pages, definitely check us out next week. From my great producer, Paul, this is Matt Heinz. Thanks for joining us today, again, on Sales Pipeline Radio.