Recruiting Sales Talent & Getting Hired: Sales Leadership Night Meetup Group

A HUGE thank you to Entelo and especially Vivek Reddy for hosting and moderating our Startup Sales Circle Meetup Group Event last week: Sales Leadership Night: Recruiting Sales Talent & Getting Hired.

2015-04-22 19.54.39Panelists:

Brendon Cassidy, VP of Sales at Talkdesk, formerly VP of Sales at EchoSign & Linkedin

Sam East, VP of Sales @ Entelo

Scott Sambucci (that’s me!), VP of Sales @ Blend, Founder @ SalesQualia; formerly VP @ CoreLogic and COO at Altos Research.

Notes & Transcription:

Below is a combination of transcription + paraphrase + summary. Good enough is good enough sometimes. :-)

What are some of the skills that are lacking in potential sales hires? What sales reps as a whole can get better at?

Sam: Sales managers generally look for the same intangibles – drive, perseverance, communication skills.

What’s missing is Curiousity – the best sales people are incredibly curious about their vertical, product, process. Really driving themselves to learning and understanding every aspect of these pieces.

Scott: Sense of strategic thinking, developing linkages across companies and your industry. From an industry conference two weeks ago, I went through all my meetings, only in 1-2 meetings where about my product and what we were selling. Most of the conversations focused on industry issues, how other companies are solving, and linking people across the industry. (Note: these were first meetings in most cases, it is was critical to develop credibility and add value to these future customers.)

Making connections raises your value and profile. Don’t worry so much about “the sale,” instead worry about “how can I help this person?”

Brendon: Have to be, especially at a startup, be both a huge optimist and a tremendous skeptic. Too many reps don’t look at risk in a deal. Being able to see the risk early, even before you get on the call with someone. A great startup sales person know where they are weak. Nobody has everything

What’s the biggest difference between “startup selling” and selling at larger/bigger companies? (10:30)

Brendon: For example, as a rep at Salesforce, you’re going to win the deal eventually. The customer has a budget, etc. It’s mostly timing. In startup sales, you have to create demand. Not a lot of people have budget for that startup you’ve never heard of.

When recruiting, I look at whether or not the salesperson has real world success at a startup – even if the startup failed, but if the rep was successful, that is a good signal. Though some might disagree with that… Maybe the rep was selling vaporware…

Scott: When I worked at CoreLogic, a company with a billion and a half in revenue, the sales process was very lockstep system for account managers and customers. Customers treated CoreLogic like a vendor (“The vendor is here…”)

From a startup perspective, you’re looking for a smaller sale opportunity, or looking for a unique problem to solve that no one else is solving, or someone that is interested in running a pilot. This gives yourself a chance to compare yourself not against competitors, but reframing and filling a gap that existing systems don’t fill. In startup selling, you’re not often selling in a big formal process but instead looking for that gap.

“You current systems are really great – let me show you have we fill like little gap you have…” Being patient. Instead of “Our CRM is so much better than Salesforce, why can’t the customers see that?” That’s the difference in selling into a niche, or creating a wedge at target customers.

Sam: At big companies, I’ve seen reps with strong organizational skills, who know their ABC in the process, have a good product, and then deliver a B- pitch and still crush it. In the startup world, that initial pitch has to be so perfect with an evangelical zeal for the product and company, and you need to be able to re-motivate when you take the knocks.

2015-04-22 19.01.54With changes to technology such as SaaS tools and big data products, how do salespeople approach the sales process differently now? How are these affecting sales and the sales process?

Scott: As a startup, you often are latest technology or at least you’re using the latest technology. At Blend, we use Amazon/AWS for cloud hosting for all of our solutions. That makes sense from a cost and scale perspective.

In our market – lenders and banks – while they are branching out and using cloud-based platforms and products like Salesforce and Workday, their core operations are still often locally hosted. The industry is still learning about the cloud and is risk averse to the cloud.

Some CTOs are still learning about “the cloud.” Early in developing our sales process, customer would would ask – “Where is our customer data? If it’s not on servers, it’s not secure.” So something we thought would be a huge competitive advantage turned out to be a detraction initially. It’s easy to be in the walls of Silicon Valley and think that everyone views technology and its deployment the same way.

Instead, don’t focus on the product and how it works, worry about the problem it solves because if you show the customer how your product solves their problem, the customers will figure out a way to learn how to use your product, use the cloud. Don’t think about your technology as feature, think about the customer first.

Sam: Sales professionals that are able to leverage sales enablement technology to the “nth” degree. At Entelo, we’re actively looking at tools and products like and Clearslide. When I see a salesperson that knows how to leverage the technology effectively without being dependent on it. Finding the right blend of sales enablement technology with the right happens.

Brendon: The reps that use technology the right ways means they have a headstart in the sales process with more and better information. Good reps avoid 2-3 painful situational calls but instead can get to the value of their solution more quickly. For example, tools like Datanyze and BuiltWith provide salespeople with so much more information than before.

Scott: There’s a crazy number of tools out there. When interviewing, bring ideas with you about sales tools that you know work. Before the interview, talk with 5-10 other sales professionals and ask them about their sales technology stack. Get introductions from friends to other salespeople if you need. Do that research, so when you’re in the interview, you can bring ideas. A lot of startup CEOs don’t know what’s out there or what to use. Maybe use Salesforce because they heard they were supposed to and they’re in San Francisco.

Even if you’re interviewing for an SDR job, bring ideas with you. There’s so much opportunity to influence the organization. Don’t feel like they know what the company is doing because they probably don’t know what they’re doing. They need ideas and that’s why they’re hiring.

Sam: It’s interesting how infrequently the sales interviewees ask about the sales stack and tools available to them. That tells you so much about the company.

What’s the best closing tool out there?

Brendon: LinkedIn to leverage and apply pressure on the customer. There’s some lever there to find. Relationships are almost becoming less-relevant but still LinkedIn is a better sales product than a recruiting product.

Sam: Taking simple actions such as clicking on profiles because it appeals to a sense of ego and vanity – “Who’s checking out my profile?”

2015-04-22 18.48.24How can sales reps go from a SDR (Sales Development Rep) or AE (Account Executive) to closing big enterprise deals? What is the one piece of advice to help a sales person to get there. 

Scott: The size of the deal changes the number of people involved with the deal. The big, big enterprise sales will get legal, operations, IT, Security, Risk involved in your deal even though they have nothing to do with the business unit that wants to use your software.

Learn how organizations function and how executives think. For example, as an executive with teams and business units below me, “How do I know they are all coordinated on the strategy that I’m pushing out there? “Or “How do I get information about what’s happening in my organization or my market?”

As an SDR, you’re thinking – “I have to get through my 50 calls today.” Maybe it would be better to think about the company, even sketch it out on paper and share it. That positions you as a valuable person in that decision and helps you as a strategic person in your com pay. Organizational behavior and decision-making – this will change your mindset and position you as an individual to take on bigger deals.

Brendon: Hire people with the aspiration to be a VP of Sales in five years. Develop a meritocracy. Start by crushing it with SMB deals, then bring the SMB reps into bigger deals over time to contribute. Sometimes the SMB promoted reps are better than the traditional enterprise reps that have the right habits.

Can be a risk if someone is thinking about being a VP of Sales when they should be focused on SMB sales.

Sam: Brendon talked about sales needing to be honest and cynical. Need to be more and more honest as the deals get bigger. Too often reps going into a deal single-threaded. They think they have the best champion in the world that’s going to “make it all happen.” In reality, you’re not realistic about that deal. If you’re not self-critical, you’re dead.

Knowing how to navigate your way around organizations. Knowing how to build multiple champions for a groundswell of support.

War stories? Tough deal? Tough time in sales. (34:30)

Scott: When I worked at Altos Research, selling data to PIMCO, a very large asset opportunities. I kept having calls and I kept telling myself that I was making progress because I kept having calls and talking to different people. I didn’t really understand how they would use our data and the difference it would make. I didn’t get to the core reason why they would use our data. I just kept checking boxes. We got to the final call – “Who is this? Yeah, we’re not interested” and he hung up the phone on me. That was it. Sale over after six months. This was my fault – I kept looking too optimistically at the opportunity and I didn’t look at the risk and I didn’t do my research on that company and that they had a history of getting . I was trying to sell too big of an idea instead of thinking more concretely about a smaller pilot or opportunity.

Sam & Brendon: Both discussed selling in 2008 and 2001 after huge market crashes and difficult global economic situations.

What the perfect length of a product demo? How complex should it be?

Scott: Peter Cohan at SecondDerivative and author of “GreatDemo!” suggests no more than three slides – Slide 1 = Situational Slide, Slides 2 & 3 are the two payoff slides/punchlines. You can always Often you get in a room with five people with the main decision-maker five minutes into the meeting gets a text and has to leave. If they’ve seen the punchline, they can say – “Okay this looks good – you guys figure it out.”

Brendon: If you’re selling a technical product to the business side, they don’t care about the gory details. Keep it 4-6 slides. For technical customers, such as when you’re selling to IT, it’s tougher to sell a value proposition because it can be a numbers game, so instead I try to focus on selling to the business side.

Scott: Treat the demo as a dual track – have the business demo and the technical demo, where the technical demo might want to spend three hours looking at every click and the code.

Sam: Be nimble enough to switch tracks as needed based on how the meeting is going. i.e. “Funny you ask this, let’s take a look at…”

How do you placate both the user needs and executive/VP level in the same demo?

Sam: These should be two separate presentations. It’s very difficult to sell to two audiences in the same presentation.

Brendon: User is looking at “Shat’s the value to me?” and the executive is looking at “What’s the value to the business?”

Audience Member: If you’re stuck with two groups in the same call, acknowledge it in the call and say – “Look, it seems we have mostly salespeople on the call, so we’re going to focus this presentation on that group. For you the executive, let’s have another call….”

Audience Member: This is a place where having a good team at the demo – say an Account Executive and Sales Engineer can play off of each other in an unspoken way to balance. Pass off and work together as a team, which can also show the customer how you work well together as a solution provider.

Scott: We call it “casting” – One person is designated to an executive and the other to the director.




Stop doing product demos

This week, I responded to an outbound sales email from a software company focusing on customer success. The last line of the rep’s email was:

I would appreciate the opportunity to speak with you for a few minutes. When would be a good time to call?

I replied:

let’s chat. I can do Wed 2:30-4pm or Thurs b/t 3-5pm Pacific

He then replied with a one-hour meeting invite, to which I replied that I could only do 30 minutes, and when we logged into the call, he was ready with his Account Executive to plow through a 60-minute product demo in 30 minutes – they even said as much – “Yeah… Usually we like to take an hour to demo our product but we’ll do our best in 30 minutes today.”

snoopy-is-joe-cool-peanuts-254005_1024_768Dude. Chill the f&ck out. You don’t even know me, my company, my problem, or why I’m interested in talking with you. And most of all, your email to me asked for a “few minutes,” and instead you’re expecting me to take an hour to watch you impress yourself with how great you demo your product?

Sheesh…. They’re lucky I did their job for them.

I took over the call – “Here’s why I’m interested in talking with you…” then I gave them the background of where we are as a company and why I replied. Even then, he kept trying to plow through the demo, like he had some kind of checklist he was required to complete in every call. I had to stop him several times just to ask questions. It’s a good thing the product looks interesting to me or he’d be dead and never know it.

So what should you do instead?

Be cool. See how long you can take a sales call without talking about your product. Even better, see how many conversations you can have with a prospective customer without showing your product.

Why do this?

As an entrepreneur, you product is your baby. You’ve identified a gap in the market, and you’ve put in the time, sweat, and toil to craft your solution.

But here’s the thing – No one cares about your product, they care only about their problem.

Until you’ve shown that you truly comprehend the prospect’s problem, you can’t earn the trust and attention of the customer to show your product. Show your product before you’ve earned that trust, and your customer will be polite, nod her head, and wonder when you will get to “the good stuff” or the part of you product that solves their specific problem.

Every customer and every situation is different. Even if on the surface the customer’s problem appears to be the one that your product solves, there is an entire base of information around that problem – how the problem developed, the people involved, past attempts to solve the problem, how decisions are made within the company, and how the problem affects this particular customer within the organization, just to name a few.

And until you have a clear view of the problem from n angles, you can’t position your product effectively or know which parts of your product are most useful for the customer.

Your solution probably has 10, 20, 50 features and functionalities, yet the customer probably only cares about 1-2 of them – the ones that most directly address their problem.

You need to qualify your prospective customer based on several criteria, because if the prospect isn’t qualified, then there’s no point in whipping out a 60 minute demo. It’s a waste of your time and theirs.

With my work at Blend, we usually require we have at least two meetings with prospective customers before we show even a short demo.

In the first meeting, our goal is to verify a critical aspects of the situation and meeting:

1. Are we talking to the right person/people? Is this person/people the one responsible for solving a particular problem we can support? Are they decision-makers, influencers, users, or simply observers to the problem? If they aren’t decision-makers or responsible for the problem, can they get us access to the right buyers at their company?

2. Validate, for both the prospect and for us, that the problem exists – that the customer knows that the problem exists and that the customer views the problem as an explicit need. The problem must be big enough to spend time and money resources to scope out solutions, and big enough to go through the changeover pain to solve the problem.

Status quo is frequently the biggest competitor, even in cases where the need is explicit. A customer has been “living with” a problem often for years (or decades!). Their patchwork solution using general technology tools like Excel or understand or other internally developed applications might be good enough for the next quarter or through the year until the next budget cycle.

3. Require that the customer to prove interest in our solution – getting them to ask questions about our solution and how it works. Asking questions about integration and implementation with current systems. Asking questions about people and resources that would be required on their end to implement our solution. Once we see that customer are thinking past just – “show me a demo so I can get out of this meeting” – then we know we have a genuine prospect sitting in front of us.

4. Learn about the history of the problem. Is this a new problem, or one that’s been around a while? What’s been tried in the past? Have past solutions include outside partners or were they home-grown solutions? Why has this problem become more urgent recently to the point that the company is ready to take action by way of people, time, and financial resources?

Summary: Figure out your qualifying criteria for your product – a good list to start with it:

  • Identify an explicit customer need, ideally enumerating it – “this is costing us $500k per month…” or “with the right technology, we think we can increase revenue by 25% per quarter…”
  • Identify the buyer type with whom you are talking
  • Articulate how this specific buyer would benefit from your solution
  • Learn the history of the problem

If you can answer these four questions, then you’ll know whether or not to bother with showing your product.

Startup Selling Lessons Learned: Confirm the “Why” of a sales presentation

The Situation:
Big meeting with a C-level executive at the top, top, top of the org chart. We’d been working with several operations managers to implement our software over the past nine months, and this meeting was set up to discuss how we might expand our work other business units.

preparationLesson Learned:
Confirm the meeting intentions and agenda. Always. No matter what the situation, no matter who the executive, no matter how much you think you know about the meeting from the most credible people around you.

We should have worked through the executive assistant ahead of the meeting – confirming the meeting and the agenda. I’m sure that the she would relayed a concise message and proposed agenda to the executive had we asked, and this could have saved us the awkward moments at the start of the meeting.

For the weeks leading up to the meeting, we relied on our own experience on how meetings like this should go and spent all of those hours interviewing operations executives. Yet we never took the time to simply connect with the executive or his assistant to confirm the meeting agenda and expected outcomes. Major fail…

What did we do right?

1. We spent several hours interviewing operations executives and managers throughout the company to learn and develop a clear value proposition at the meeting. We even spoke with an employee that recently left the company to learn what we could from an insider/outsiders perspective.

2. We were super prepared for the presentation, enabling us to quickly dive sideways in the presentation when the executive took us off of planned track. We had planned ahead to discuss all of software applications that were used by the company, not just the application that was the intended focus of the meeting. This proved to pay huge dividends for us.

Here’s how it went down…

When the executive we were meeting arrived to the conference room and sat down, and we began our introductions, he stopped us, looked around, looked at his phone and asked in the most honest way – “Who are you, and why are we here?” It wasn’t asked in a challenging way as happens with some executives that want you to get right to the point. He honestly did not know why he was in this meeting other than the fact that his assistant told him he was supposed to be here right now.

Even though, as we understood it, he was the person that had asked for the meeting several weeks ago. In fact, we were scheduled to meet the week prior and he pushed it back a week.

We had spent most of the past week developing our presentation – thinking through the economy of slides – what to show that matters most to him, interviewing professionals across the company about they thought he would want to see and what he cared most about. Our design teams worked extra hours to provide us with beautiful screen shot mock-ups to impress him. My colleague leading the project spent Super Bowl Sunday in the office by himself on final presentation preparations.

And now, all of that now completely obliterated.

Disaster-Recovery-PlanThe recovery,,,

First, I laughed a little (to myself).

Then I started over, as if he had been teleported to this room from another planet, and I had to explain my reason for existence – who our company was and why our our understanding for the purpose of the meeting. Together, we discussed our “Situation Slide” (which I highly recommend preparing – thank you to Peter Cohan at SecondDerivative for this powerful tip…)

When I did that, the executive seemed uncomfortable with what I was saying, so I asked – “Could I ask what’s frustrating you?”

He explained that he didn’t necessarily agree with a few of the assumptions I was making about the company’s intentions and objectives.

So I asked him to explain which parts exactly. Voila! Conversation started. Even though the conversation and presentation immediately drove off the rails from what we intended, the “Situation Slide” created the opportunity for conversation and discussion.

From there he shared his views about the particular situation we planned to address, and most importantly, he told us what he most cared about, and it turns out his major focus was not for the business area that we had prepared to discuss.

Eventually, we got into the presentation – skipping around from our plan, showing what was most relevant from his perspective, and even moving off-script to walk through a completely different software application than what we prepared to show. The meeting was scheduled to run an hour, and we went 20 minutes past that. We ended the conversation with the executive suggesting that we should be in consideration for a significant open RFP for one of the business divisions.

You might ask – “Hmmm…. Good save, but why didn’t you confirm the agenda and outcome with this executive ahead of the meeting? Why didn’t you do a pre-call?”

Valid questions. My reasons, though not good ones, and why this is a lesson…:

Firstly, the meeting was originally set up for us through another C-executive at the client, and we were told directly by the first executive how important this meeting was for this executive.

Secondly, this executive is at the top of the org chart – you literally can’t go any higher than this person. I allowed us to feel intimidated by this, and instead discussed the presentation all around the executive assuming this would prepare us accordingly.

Lesson learned…