I did my 10 sales calls and a funny thing happened

IMG_504415 total calls:

  • 10 new outbounds
  • 3 calls resulting from previous outbounds and referrals.
  • 2 calls with previous customers

The results?

  • 1 actual sales call in which I was selling
  • 1 voicemail message left
  • 5 future meetings set up by emai, beginning today, all resulting from my new outbounds.
  • 8 no responses so far
  • (Note: 2 people that I outbounded earlier this week checked out my LinkedIn profile.

How it went down…

Got started in the AM with two easy outbounds – people I’ve worked with in the past. I’ve needed to schedule time with them for a couple of weeks (shame on me…). I sent emails, and both got back to me within a couple of hours scheduling calls with them this week/early next.

Off and running!

I later had a call with a startup CEO looking for help on his sales presentation and product positioning. The more we talked, it occurred to me that he was an IDEAL candidate for Startup Selling. So that advice call for him turned into a sales call for me. Okay, call #3 in the books.

Then I called an investor that replied to a LinkedIn Inmail I sent on Sunday. Not a new call by my criteria , but I did make a call. Voicemail. Then I followed with a text message to see when we might talk. No response yet.

Next, I confirmed a call for today with introduction from last week.

Check. That makes five, except that none of them were true “new” outbounds. and now I was stuck. Stuck doing other “stuff,” and feeling mildly depressed about it.

I needed a push a little luck. And I got it…

It was almost 3:30pm and I wasn’t getting through my ten new outbounds. I hadn’t even done ONE new outbound. Worse, I had a 4:30 call scheduled, and I was dragging on energy.

The push

I grabbed a box of business cards sitting on my shelf. I had no idea want I’d find in this box – it’s been at least a year since I even thought to look.

My thinking? Just do something related to selling, even if that meant cold emailing people I met at some event a year ago. At least it gets me in the act of selling. Boom! Let’s go. I headed to my favorite coffee shop where the atmosphere + a double espresso = Productive Scott.

I started hammering. I first emailed the former director of Venture Greenhouse, who hosted me to do a sales workshop as part of Startup Grind two years ago.

I emailed a head of Fledge – an incubator program in Seattle. I met him two years ago during a visit there.

I emailed a local sales executive (Dave) that I thought would know a referral or two that would be good candidates for Startup Selling.

Ugh… Then it was 4:30. I still wasn’t getting to my ten, with or without a double expresso.

Then a little luck

The meeting I thought was at 4:30pm was in fact on a different day, opening a window to keep hammering.

I emailed a startup CEO that’s built a marketing platform.

I emailed a Salesforce executive that has a couple of side projects. Then I emailed someone I know that works at a company solving the same problem as one of his side projects.

I emailed two random people I don’t remember meeting but had their business cards. Why not? Check, check, check.

Then Dave got back to me and introduced me by email directly to a startup CEO friend of his. I emailed the friend, and after some back and forth right away, we’re set for a conversation on Friday.

Then I received some sales manna from heaven. After proving to the universe that I was willing to push, I was rewarded with an inbound lead from my website.

(I have a page on the site on which people can schedule a time to talk with me about Startup Selling.)

Best of all, the inbound lead is from a really, really interesting company in the FinTech industry – super interesting lead based on my experience over the past decade selling to banks and financial market companies.

Then to wrap up the day, the marketing platform CEO got back to me. We’ll find a time to talk next week.

I did my ten. Did you?

Can you do it? 50 sales calls in 5 days

50 sales calls in 5 days.

I bet you can’t do it. They don’t even need to be phone calls. Try using InMails or personalized emails.

My results this week so far? Shameful.

Sunday: 8
Monday: 8
Tuesday: 0
Wednesday: TBD

AND THIS IS WHAT I DO FOR A LIVING! I teach startups how to build their sales process and I’m not getting to my ten sales calls a day. So embarrassing.

Selling is hard. It’s painful. Picking up the phone is different than saying – “we’ll just sell to product managers” or “we just need to get in touch with IT directors” or “once we get a conversation with the VP of marketing, we’ll be able to sell to them pretty quickly.”

Like every CEO, I get busy working on product. And marketing. And recruiting. And finances. And managing the company. Days ticks away like minutes. Hours tick away like seconds. I get tired, I get frustrated, I get lazy.

If I get tired and frustrated and lazy, I know that you do too. It’s okay. Selling requires time and focus and concentration.

You probably have ideas about the companies you think your company should target, and you probably have ideas about the people at those companies that you think are buyers.

And your ideas are probably wrong. That’s exactly why you need to start selling today. Right now.

Check your January forecast. What were your revenue expectations for the year? Are you on plan? Why are you falling short?

Maybe deep down inside you know you could be wrong about your market and your product and your business model. Or worse, you’re so confident in your ideas that you have unknown unknowns just waiting to blow you up.

And I bet this is why you’re not hitting your sales goals.

When you sell, you learn stuff that you can never, ever learn building product or raising capital or tweaking code.

Selling reveals the unknown unknowns – gaps in your product and gaps in your value proposition. It reveals that your customer has a buying process that doesn’t match your sales process.

So start selling. Today. Right now. Pick up the phone. Make one call, and then another, and then another. See if you can get to ten by the end of the day, no matter what.

Heck, you might not even have 50 people on a list right now that you can call.

You probably have a pile of business cards from a recent conference. You probably have a few emails buried in your Sent folders that need you to try again. Start there. Whatever you do, just start.

Ok… gotta run. I’ve got ten sales calls to make…

(If you want a little help, check out Startup Selling. I built it just for you.)

10 Sales Email Strategies & Tips


Is anything more frustrating than sending a follow up to a prospective customer only to get nothing back in reply?

Use these ten tips for sending emails to your customers and I guarantee you’ll get more replies and more follow up meetings, and close more deals.

1. Always end your email with a question.


  • “So can we plan for a call on Wednesday next week – would that work for you?”
  • “Would you please reply back with Sally Jones’s contact information so that I can give her a call?”

2. Suggest specific times in your email for a meeting.


Hi John, Per our conversation last week, you wanted to set up a time to talk with your IT team about configuration planning.

Here are a couple of times that work for me (all times US Pacific): Tues (7/21): 10-11 am, 1-2 pm, 3-4 pm PT Wed (7/22): 9-10 am, 4-5 pm PT Thur (7/23): 10-11 am, 2-3 pm, 3-4 pm PT

Anything in there work for you and your IT manager?


3. View a draft of your email on a mobile device.

Send a draft to your personal email and see how it displays on your mobile phone.

Remember: Even when your customers are in the office, they’re in meetings or walking around, checking email on their phone, not on their computer.

4. Use specific subject headings.

Craft these based on the situation and where you are in the sales process. For example, once I’m in a good cadence with a prospective customer, I use email almost like text messages – asking specific questions or confirming.


  • “Can I give you a call this afternoon?”
  • “Confirming for our 2 pm call this afternoon”
  • “Did you receive the WebEx info I sent over?”
  •  “Should I give you call?”
  • “What’s the best time to reach you?”
  • “Are you attending the XYZ Conference next week?”

5. Use “RE:” in your subject line, even if it’s the first email in the chain.

This signals to the customer that this is a continuance of a conversation. Even if the “conversation” was as simple as their filling out a lead form on your website or from a meeting you had with them last week at a conference.


  • “RE: setting up a call with the team”
  • “RE: info security requirements”
  • “RE: heading to the MBA conference next week”



6. Send a LinkedIn connection request the day after your email.

  • Do this ONLY if you’ve made contact with the person and have developed a relationship with the person.
  • Then, PERSONALIZE the LinkedIn connection request
  • DO NOT use the “I’d like to add you to my professional network on LinkedIn.” standard message.  Use something like:

Hi Amy – Many thanks for the time and call this week. Looking forward to scheduling our next call with your Product team. Thought we might connect here on LinkedIn in the meantime…

7. Copy (“cc”) someone else on the email and mention the person you’ve cc’ed.

Hi Roger – Really glad we met last week at the conference. I enjoyed the conversation and I’m looking forward to introducing you to Jonathan Marks, our VP of Engineering (cc’ed here).

You mentioned that next week would be best for a call. Here are a few days/times that work for us: Tues (7/21):

Any time 10 am-12 noon PT Wed (7/22):

Any time 2-5 pm PT Thur (7/23): 10-12 am or 2-4 pm PT

Anything in there best for you?

Thanks, -Scott

8. Give yourself permission to follow up with a call in two days.


Hi Roger – Thanks for the time this morning on the phone. I appreciate you sharing more about your company and the challenges you have ahead on the mobile side of your business.

Per our conversation, let me know what works for putting together a call with your engineering team so they can ask questions about our platform.

Just reply back to this email with a couple of times. I’ll give you a buzz on Thursday if I don’t hear back from you by then.

Talk to you soon!


9. Send a separate email with a news article, blog post, video, or some other content related to the discussion.

This adds value to the person while nicely prompting them to get back to you on your previous email.

Example: “Hi Ben – I just came across this article on…”

  • ProTip #1: Sign up for Newsle. It scans the news every day for you and notifies you if any of your LinkedIn contacts are mentioned in news articles and blog posts.
  • ProTip #2: Set up a daily Google News alert for the company and key topics within your industry.
  • ProTip #3: Sign up for 3-4 daily newsletters from industry publications. All three take the work out of researching and finding articles to send to your prospects.

It takes just a few minutes to scan the headlines delivered to your inbox. Then you can copy and paste into a new email to selected prospects.

10. Email 1-2 days after your first email with a follow up question or a mention of their work.


  • “One more question…”
  • “Something I forgot to ask…”
  • “Do you know [insert name]?”
  • “Forgot to ask…”
  • “Just talked to [insert name]”
  • “Just watched your presentation at the Tech conference”
  • “Just read your guest article on WSJ.com”

Awesome! Now you’ll get more replies to your emails, set more next meetings, and keep moving your sales opportunities forward. What now?

  • So how do you prep for those meetings?
  • How do you achieve the optimal outcome from your product demos?
  • How do you know you’re talking to the right person?

Sign up for our updates and receive a slew of checklists you can begin using right away!

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 InsideSales.com 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.




SalesCast #2: Be a Connector… of people & ideas [podcast]

connectorThis is short podcast (only 8 minutes!) recorded from New York City in which I talk about the value of being a connector of people and ideas with your current and future customers.

I attended a conference on behalf of my work with Blend Labs, and in reviewing my day of meetings, I realized that most of my conversations didn’t focus on Blend’s products. Instead, the conversations focused on ideas and people where I could support our future customers.

Add value, add value, add value…


SalesCast #1: Startup Selling with Conference Escorts (sales podcast)

In this SalesCast, Robert and I talk about “conference escorts.”

WingmanWe discuss how to set meetings at a conference, executing on those meetings, and following afterwards. Throughout the conversation, we talk about lots and lots of practical strategies – everything from using “InMails” on LinkedIn to sending meeting confirmations via text to roles (or “casting”) in a meeting to using questions to land more meetings.

Detailed Show Notes:

Intro: This SalesCast is brought to you by, well, SalesQualia. Improve Sales Performance with:

  1. Self-learning resources, including books on Amazon.com and self-paced online courses.
  2. Workshops & Training, hosted at venues across Silicon Valley and the US.
  3. 1:1 Coaching & Consulting for company founders and sales professionals that want a personalized plan.

2:30 – Introducing “conference escorts” and what this person does for startup founders & entrepreneurs at conferences and live events.

5:32 – Using multiple people in a meeting to facilitate conversation at a conference meet-and-greet conversation.

7:08 – Roles & casting for meetings. How to position each person on your side in a meeting based on person you’re meeting.

9:00 – Using ambiguity to your advantage. Having the second person on your side as a “wild card” in a meeting to allow for flexibility in the casting for a meeting.

11:18 – Positioning yourself as a business conference escort and setting up meetings for startups.

12:20 – Using “customer development” to your advantage to landing meetings with executives

13:30 – LinkedIn & InMails to set conference appointments

16:00 – Results using LinkedIn & InMails to get 25-40% response rates for conference meeting requests instead of emails.

18:30 – Why using conference escorts might be a good idea for a startup founder/entrepreneur

20:20 – How much time should you plan to spend setting up appointments prior to a conference?

21:30 – Approaches and research for sending effective InMails and appointment requests

24:00 – Helping an outside sales consultant to get up to speed with your product and value proposition

25:30 – Managing responses to meeting requests for conference meetings

26:00 – General time and budget allocation pre and post-conference. Pricing out a conference project with a sales consultant. Setting up incentives and setting baseline expectations.

30:30 – Building a conference escort team. Who do you hire? How do you build a team? What to do if the startup wants to hire a conference escort on a full-time basis?

33:30 – Finding talent to help with customer development at conferences including part-timers and established business veterans.

36:15 – Breaking down the stages of conference meeting development – pre-conference, at the conference, and after the conference.

38:20 – Tips for sending meeting invites for conference meetings. Confirming appointments.

39:30 – Ideas for finding conference [business] escorts

42:00 – Using people only for the conference itself, not pre- and post-conference follow ups.

44:18 – Post-conference follow ups. What to do after the meeting? How to pull these meetings through to be real sales leads? Avoiding the dead space after conferences.

47:30 – What to do if you met with someone that isn’t a decision-maker?

50:00 – Revisiting success metrics for conference meetings. Defining a quality meeting with four (4) success metrics.

54:00 – Identifying gatekeepers & heros vs a true partner at your prospect

56:00 – Wrap up and summary

Here’s a link to the podcast one more time…

Your customers are lazy cows & it’s not their fault


Cows don’t know any better. They wake up, they eat grass, they walk along windy, crooked paths simply because some cow before them walked that long, windy, crooked path.

In a company or organization, this is called “path dependency.” Microeconomic research also shows that humans are generally risk averse. People have an aversion to taking risk and maintain a “status quo bias” – they desire for the current status even when a proposed change will improve their situation in the long run. Anyone that’s worked for a big company (or even a small one) has heard – “I don’t know. That’s just the way it’s done around here…”

As an entrepreneur or salesperson with a new product – one that will absolutely improve the situation of your prospective customers – how do you deal with this reality?

As the keynote speaker at last night’s Sacramento Startup Expo, I suggested to the audience that they focus on two things:2015-04-06 19.56.05

1. Give your customers a specific reason to make a change. It has to be more than just the standard – “Our product will decrease your costs by 35% over 12 months…” or “Our customers have experienced a 55% increase in efficiency after implementing our solution…”

Find a way to connect with person and team making the purchasing decision. What is their personal motivation? How are their personal goals and incentives aligned with your product?

As an example, imagine your buyer is a newly appointed division head While she’s probably looking for ways to increase output and run the business more efficiently, her personal motivation might be to find ways to score quick wins in the first 90 days to prove to her managers that they made the right decision in hiring her for the job.

  • Could you align your solution with her short term needs to find quick wins, instead of selling a long term solution that might take months to implement,
  • Are there high value problems in the business unit that your product addresses immediately?
  • Could run a pilot program at a low economic cost to her so the decision stays local, and if successful, she can then show her managers who she is immediately impacting the business?

By keeping the implementation small, she wins if the pilot is successful because she looks like a hero. And if the pilot fails, she need not worry about losing face with her superiors early in her tenure.

2. Motivate your customers to take action by demonstrating a clear implementation plan. Show your buyers how purchasing and implementation process works when they buy from you.

For example, build a “7 x 1” framework, thinking in terms of “first” time period intervals to show your customers specifically what happens when they purchase from you. These intervals are:

The first minute…
The first hour…
The first day…
The first week…
The first month…
The first quarter…
The first year…

What would happen the very first minute that your customer gives you the green light? Would you inform your engineering team to begin implementing immediately? Would you set up a conference call with the customer’s chief risk officer to discuss the implementation plan? Would you set up logins for all of the users covered by the license? It’s different for every product and every customer, so think about what should happen this very first minute for each customer.

Further, after the first hour, what would have happened? Do you call the customers IT department to discuss support systems? Do you schedule travel for onsite training? Do you contact the finance department to arrange payment specifications?

By the end of the first week, should you have finished training and have your first users logging into your software? Should you be rolling out your software with the customer’s satellite office in Tacoma?

It’s up to you, your product, and the customer as to what happens. This will be different for every situation.

Following this “first” interval thinking and share your plan with your customer, gives them the confidence they deserve to know what you’re doing. This also builds trust and presents the opportunity to develop this plan with the customer. Maybe the customer says – “Hmmm….. rolling out to the Tacoma office after the first week is a little aggressive. We should do plan that for week three.” Great! Now you have buy in from your customer and they become your partner in the sales process to push through this decision.

Help your customers find new grass in the pasture by giving them a reason to take action with a clear plan.

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.

Don’t take a dump in a box and mark it guaranteed


I was talking with the sales rep from a telephony company yesterday. She said:

“We have 100% guaranteed up time. For every 10 minutes we’re down, we refund you 1% of you monthly bill.”

Then her line went dead…

I had someone this week ask me, that as a startup, would it help find prospects get off the fence by offering a guarantee?

No. It won’t. You’re a startup. If your product doesn’t work, you’re going out of business and the guarantee won’t matter anyway.

Moreover, there are the switching costs your customers incurs. It might take days or weeks or months or more to completely implement your software or product depending on the complexity. The president of a very large mortgage lender told me that it took five (5!!!) years to fully implement a loan origination software system. Five years. Five F&*CKING YEARS! He can’t go to his Board and say – “Yeah, but don’t worry if it doesn’t work out, we get our money back…”

The telephony company with their 100% up-time guarantee and 1% refund policy… They charge ~$100/month for their service. If a call goes dead when I’m in the early stages of a $100k sales opportunity, I don’t care about the $1.00 refund for their six minutes of downtime. I care about the $100k deal and $10k commission I lost before the deal ever got started.

Retail companies like to say things like – “If you find the same item at a lower price within 30 days, we’ll refund you the difference.” Yeah, sounds good. But am I going to drive 15 miles back to Best Buy in the hopes that they’ll give me the $20 price difference between the camcorder I bought there and Fry’s new advertisement? Unlikely. (Not to mention all of the stipulations.) Don’t pretend you care about your customers with a guarantee. It’s a lie. You know and they know it, and they know that you know that they know it…

Instead of guarantees, make implementation planning part of your sales process. Give your prospective customer a reason to trust you. Show them early in the sales process what you’d do the first minute the contract is signed. Then the first hour. What would be accomplished by the end of the day and in the first week – setting up logins, working with the customers IT team, delivering onsite training, measuring the impact of your software against the very same metrics you’ve been selling on.

If you tell your customer they’ll be 28% more efficient with your product, show how you track this metric starting on week one, and what you’ll do by the end of week two if they’re not starting to see those gains.

If you tell your customer they’ll reduce costs by 75% over 12 months, show them how they are on track to reach those cost savings at the end of first month, and what you’ll do to remediate if they’re not on track.

Tell that that you will sit side-by-side with their users every day for the first week to make sure everything is working perfectly.

Skip the guarantee and show you’re customer how much you will love them.