Startup Lessons Learned: Sales Strategy – Shut Up & Save a Sale

Sales Strategy: Shut up and sellHave you ever been in a situation where you or a colleague keep talking after your prospect or client has already decided to purchase? I know I have been. If you don’t read on you could snatch a “no thanks we’re not interested” out of a sure sale.


What reminded me of this was a recent trip I was on. I had to go through Paris several times over a 2 week period. So on the first trip out of CDG, I met a taxi driver who seemed great – clean, nice car, good driving skills and pleasant. I told him I had several more trips in and out of the airport as well as trips within the city. He eagerly gave me his card and told me to please use him for all the rides. I told him I’d take him up on it. He just got a nice sale!

A few days later, there he was right on schedule to take me to Orly airport. It worked out great, I got to know him a little better and found he was a well educated guy with a nice family. At that point he was batting 2 for 2 and looking to get lots more fares. Then…it happened. On the pick-up when I returned to Paris, he messed up my arrival time and ended up sitting at the airport for 2 hours. His first words for me were “you told me the wrong time!” Who doesn’t use their phone to confirm flight times these days anyway? I told him to check the email and txt threads, where I had clearly communicated the exact arrival time & gate info. He argued a bit then wisely let it go. Thank God.

I was ready for a calm ride after that and would have let it all slide and continued to use him. I understand that time lost is money lost. But nope, he had to do it, yep, bring up politics, and went so far as to say “how could you ever vote for a woman to run your country?” Needless to say I told him not to go there, but he wouldn’t give up. He kept pushing the issue to places where I just got fed up. I mean, at the end of the day I don’t need a debate on my taxi ride, I’d really rather catch up on business emails. When he dropped me off, I let him know I wouldn’t be needing his services any more. He lost a a big sale & good amount of certain income. F for his sales strategy.


The flip side, years ago I was at a well funded start-up and we were interviewing PR firms. I was meeting with the last company, and was so impressed hired them on the spot. After telling him to shoot over a contract and other docs, I’d never seen a guy wrap up a meeting so fast! He immediately stood up, said thanks, rounded up his team and bolted out the door. I talked to him later about it, and he said “what good would it do, at any time someone could have said something to screw the deal?!” Great point. He knew when to shut up. Great sales strategy.


Recently I was reminded of this very important lesson that should be ingrained in all of us. I was speaking with a client who was having some issues with our app – it just wasn’t fitting her needs which were very specific. We’d had a very productive call, she was happy with the fixes and the timelines. Done deal! But for some reason I got excited and and started to mention a couple of ‘stretch’ features we’d been contemplating. All it did was highlight some weaknesses in our current offering, which made her think about other features we might not have yet. Needless to say I caught myself early on, did a bit of a dance and reeled it back in. But whew! Not knowing when to shut up can cost you! When the deal is done, wrap it up.
Have you ever muffed this sales strategy and talked yourself out of a sale? Let me know your experience!

Startup Lessons Learned: The Culture of Customer Success

I love Italy, my wife and I enjoy visiting every year. There’s one thing – in addition to the awesome pizza – that astounds me about screen-shot-2016-09-16-at-4-39-47-amthe country; the culture of service. It got me thinking: in this day and age of doing everything in a faceless business world, how can you have great service and ‘customer success’?

On the Isle of Capri there is a wonderful wine bar, Capannina Bar, it’s been there forever. It’s one of the only places open all year round. The island closes to tourists November to March so the locals need a place to go. On a recent visit, we were walking down the tiny street and we saw our friend Benny who is the bartender. She was delivering glasses of wine and chips to a local store owner for them and their customers. Wow, that’s double service, not only is Benny serving the store owner, the store owner is ordering wine for their customers. And it just comes natural to them. Try ordering a ‘to go’ delivery of drinks from your bar and see what happens!

What To Do?

As a business who develops apps we unfortunately don’t have a bunch of Bennys around. So how do you go above and beyond expectations to service customers who you may never talk to let alone see? It’s vital to instill a culture of customer success.

Here’s what we focused on at Dasheroo:

  • Alf, our VP of Customer Success, answers emails fast! Expectations these days are, you get an automated email then in about a day you might get someone to get back to you. Not Alf, he knows data is important to make decisions and people need answers…fast. We use Zendesk.
  • If anyone wants to talk to us we set up a Grasshopper phone system (cheap!) and it’s so flexible. You can forward to a live phone within certain hours or only allow folks to leave messages. When someone leaves a message an email is sent to multiple people so we can get back to them fast. Mimi, our Sales Director is like lightning.
  • Alf proactively reaches out to people who seem to need some help with Dasheroo (they created an account but are inactive) with Calendy. They can schedule time with him to go over any questions they have and make sure they get the most value from Dasheroo!

What is your service culture? Please share!

Startup Lessons Learned: Can You Be a “Friendly” Boss?

startup lessons learnedI was recently spending time with a good friend of mine, he’s a hot shot professor of design in Switzerland. Tom also has his own design firm and had just brought on a couple interns. He was talking to me about an issue he had with them.
Tom had invited them out for a night of fun – drinking & dancing to a well-known DJ going late into the night. But there was an initial agreement. If he allowed them to join him, that the next day they needed to deliver some initial design comps for a new product line. And…they kind of dropped the ball. Our buddy is a very nice guy, and was feeling frustrated about the line between ‘friends/friendly’ and being an effective manager.
It brought up a dilemma many managers face – can you be friends with your employees? My buddy Kevin O’Leary (Shark Tank, Mattel) says “your employees are not your friends” and I get it. It can remove objectivity and jeopardize your business decisions. But, if you already crossed that line, how do you manage this issue to success?
It’s actually very simple in theory, but 100% necessary to execute, especially if you are a ‘friendly’ type of manager:
  • Establish clear goals from the beginning – don’t beat around the bush
  • Lead by example – have fun but get your business shit done
  • Address & resolve any issues immediately – nip any issues, even if they seem minor, in the bud. Once you let something slide, you are on your way to failure. Your employees deserve to know your thoughts so they have a chance to improve.
  • Establish boundaries and if they re not respected you have the wrong people, friends or not
  • And, if it isn’t working, take the hit – fire if necessary. BUT take a close look at yourself and change your management style. Because it’s all about Business First.
Hey, I’ve lost friends because I had to fire them, and wish I would have never hired them in the first place. So don’t misplace friendship for objective business decisions and for new folks you hire, it’s OK to be ‘friendly’, but watch that line!

Startup Lessons Learned: Don’t Underestimate the Power of Video

This week’s startup lesson learned will be short and sweet. It’s about video. A lot of folks think that video marketing is hard and that creating videos takes a lot of work and money. Well, that’s just not true! While it does require time and effort, it really can both make and save you money.

And it’s not only about going viral on YouTube, in fact here at Dasheroo while we have our own YouTube channel we use videos for a variety of uses.

Here’s how we roll:

Support Videos

Dasheroo YouTube Analytics

Our Google Sheets integration gets a ton of views, digging in we made a few additions to the feature!

We have some features that can be a bit advanced for some users. Creating a step-by-step video for them to understand how to use a specific feature is critical to getting usage of our application. We look at Total Views in our Dasheroo YouTube dashboard so we see what features are most popular. Those features might actually need more work since what we offer might not be intuitive or useful enough.

This is a huge money saver since we don’t have a big support team to handle questions, and users can access the information whenever they need it.

Marketing VideosZapier Dasheroo set up guide video marketing

Alf creates videos for some of our partners so they can put it on their site to get the word out about our integration. This one he did for Zapier got a ton of views and it really helped Zapier market our integration as well, bonus!

He’s also done a “3 Minute Tip: Stocks on your Dasheroo Dashboard with IFTTT & Google” which was a fun way to use your dashboard with 3rd party products.

We love his videos, they’re personable and short, we try to keep them under 3 minutes. Alf uses Screenflow for that and it’s only $99. It has lots of bells and whistles but is still easy enough for anyone.

This is a money maker since we do get some SEO juice from the videos and we do get new users from our awesome partners who post and share these videos.

Internal Videos

Josh creates videos internally to show us a new feature before it’s live. It’s been hugely helpful for both his product team and the rest of us as we get ready to market and sell. Josh uses Jing for that and it’s free up to 5 minutes of video.

We also outsource tasks to a virtual assistant group (VA Staffer) and we create how-to videos for them. It’s great since we only really have to create the video once. In the event one of our virtual assistants is on vacation or out, we don’t have to get on the phone for a training again. They just refer to the video.

These are enormous money savers. Why? Time is money and we have neither to waste!

Startup Lessons: The Power of a Single Positive Mention

Here at Dasheroo we’re increasing organic traffic and signups each month with zero paid media. It’s a combination of our freemium model, solid SEO and inbound marketing, and what we hope is a great product and user experience that people will share. We’ve also done a ton of influencer marketing to get our product off the ground and continue influencer outreach. We track our activity very carefully, and can pretty much plot our growth trend.

But all that said, it’s awesome when we get an unexpected – and very much appreciated! – mention from a big influencer. In this case, it was from our friends at Social Media Examiner. Talk about an influence, their blog and email reaches hundreds of thousands of marketers and is very well read and highly respected.

The article was How to Monitor Multiple Social Media Metrics in a Single Dashboard and we were fortunate to be the first of four options they recommend:

Dasheroo article from SME resulting from influencer marketing.

The power of a single positive mention!

On that day, August 8th, and for several days after that our new user signups went through the roof:

Dasheroo new users from influencer marketing!

We estimate that that one positive mention drove almost 1,000 incremental new users. And of course it’s not all about new users – our signup conversion rates doubled! We also saw an immediate spike in sales and agency leads for Mimi, our agency salesperson, to follow up on and close.

Lesson learned: Work your ass off and do good things, people will talk about you and stuff like this can happen! Influencer marketing is no joke.

Next, we’re making sure to run cohorts on this audience segment to carefully track how they convert and retain over time. This will help inform us as to the audience match, product focus and potential of partnering with them on future activities.

Startup Lessons Learned: Customer Segmentation Exercise, Fun!

The other day, I realized with all the hubbub that happens in our small & growing startup Dasheroo, that I had lost touch a bit with just whoour customers are. Sure, I could talk about “here’s how many we have, this % are agencies, that % are consumer brands, here’s the ARPU and this % are outside the US” type crap, but it bugged me I hadn’t done a deeper dive for awhile.

Dasheroo customer segmentation research in Google Sheets

I put our customers into Google Sheets on my Dasheroo dashboard so everyone could see!

So on yet another gorgeous San Francisco day I hauled my dog Dwight, a beer and my MacBook out on our patio for a little customer segmentation project. I took 100 random paying customers that are from our ‘sales assisted’ category, meaning they pay us enough $$ to have a sales person work with them, as opposed to our lower ARPU ‘auto convert’ biz. Not saying the auto convert biz is in any way less important, but I needed to focus where to point or limited resources for outbound sales efforts.

One by one, I hit their websites and built on a Google Sheet with a simple ‘who – where – what’ layout; the customer name, where they are based, and what type of business they are.

OK, maybe it took a beer or so more to complete but as I progressed I got more and more excited. I mean, it’s so easy to go from one sale to the next, always focused on ‘the next’ that you can begin to miss some key trends and customer profile types.

In this case, a few really interesting, and I hope actionable, trends were spotted with my customer segmentation research:

  • Agencies that target the SMB market. Regional in nature, and a good concentration in the Southeast US and Australia
  • These agencies aren’t ‘we’ll do everything for you’, a huge % focus on social media and influencer campaigns and measurement only.
  • A few decentralized departments of pretty large, well known consumer brands.

So what? Here’s what: we’re gonna re-focus our lead gen budget with these geos and a closer match to the ‘social media’ agency markets vs. a more broad targeting. Next, we’re thinking about launching an outbound effort to “land & expand’ to grow within the large consumer brands, working our way across geographic departments first and hopefully further across functional departments within each location!

Sure, I could have ditched this project off to someone else. But sometimes rolling up your sleeves and getting your hands a little dirty with customer segmentation can really help put your focus back where it matters. Next, a similar exercise with our auto convert buyers!

Startup Lessons Learned: Park Your Ego For The Success of Your Business

I caught up with an old friend of mine the other day, he’s the chef of a restaurant here in SF. He seemed pretty stressed and told Check Your Business Egome about a big issue he was having with his business partner.

My buddy Brad had recently hired a new sous chef against the wishes of this guy (who doesn’t know much about the restaurant biz.) The partner had a long time friend he wanted to put in that position, but Brad just didn’t get a good feeling when they met, and he had what he thought was a great person for the role.

The discussions got pretty heated, actually almost to the point of a split. Brad was supposed to have operational control of anything in the kitchen, so he made the move against his partner’s wishes.

At that point the partner threatened to back out, shut down the whole place. He was so incensed and couldn’t rationalize or accept that Brad knew what he was doing. Brad knew how to operate a restaurant let alone a kitchen, he’d done so successfully before, more than once.

Brad seemed to have made the right choice – recent Yelp reviews were very positive, the kitchen seemed to be operating smoothly and the new guy was also good at controlling food costs. But the owner just couldn’t handle the fact that Brad was in the right, knew what he was doing and knew more than him about the business.

So now, the partner IS backing out, leaving Brad to find new investors or shut down his restaurant. All because he let his own ego get in the way of something that really could have been successful.

My lesson learned? NEVER let ego get in the way of success!

Startup Lesson Learned: Shhhh, You Never Know Who’s Listening!

lesson learned - DasherooThis lesson learned isn’t one of those “if you’re always talking you never listen or learn” posts, although that is worth repeating. Nope, this “lesson learned” is more along the lines of “just shut up” when you are talking about other people, companies or deals. Sounds obvious, but I think we all slip into complacency from time to time.

Just in the past couple weeks, here’s a few:

  • 2 senior-level seeming guys talking over lunch about firing one of their VPs, referring to him not by first name, but by last name. It’s an unusual last name, and a tiny bit of listening confirmed that they were talking about an ex-coworker of mine! Did I give him a heads up? You bet.
  • A friend of mine talking to me on the phone about his CEO. Nothing super negative, but he was voicing a little frustration while calling him by first name as he was walking near his office, rounded the corner and BAM! the CEO’s executive assistant was standing there smoking a cigarette. Awkward at best…a job lost at worst.
  • I was with a group of people at a restaurant talking about a potential deal with a well-known public company, based right here in San Francisco. Last names AND the company name got mentioned a time or two. I freaked out!

Lesson learned, or at least remembered? Use first names, not last or full, and never mention company names. There are ears everywhere, and one ill-placed comment can damage or tank a relationship or deal. Don’t do it!

Startup Lessons Learned: Testing Facebook Ads

Dasheroo for Agencies - KPIsRecently we needed to drum up some leads for Mimi, our Director of Sales here at Dasheroo. Where did we turn? Facebook Advertising of course. How easy is it to set up a Facebook Ad in minutes, get it approved in minutes and start to find out what works and what doesn’t.

So we started spending a mere $20/day to drive leads to a sign up form where people can get more information on Dasheroo for Agencies.

Facebook Mobile Might Not Work for Your Offering

If you’ve got an app that appeals to a mobile audience, include placements on Instagram and Facebook Mobile. You should even set up separate ads so you can track each of them.

At Dasheroo we were getting a TON of traffic but no conversions because we selected our ad to be shown on Instagram and Facebook mobile.

Dasheroo Google Dashboard

So make sure you track where your website traffic is coming from. In this Dasheroo Insight we track Google Analytics by Device type. Just before the 16th of May you can see that our mobile traffic eclipsed our desktop traffic…weird.

Facebook Automatically Checks “Audience Network”.

This means that your ad will be optimized for where it will get the most bang for your buck. However you might not get conversions from it. And that’s what happened to us.

From the graph below you can see that Facebook looked at the Cost per Result and found that the Audience Network was giving us a .08 per click. Nice but not when they don’t convert. And we found people were not converting from a mobile device. Less than 1% of our traffic was going to the desktop. Even though that Cost per Result was .54 cents they may have signed up for more information.


Facebook Ads Analytics

So now we went in and unchecked Audience Network!

Screen Shot 2016-06-28 at 6.53.39 AM


Now we bumped our spend to $40/day. We’ll blog again when we see if there were any changes in conversion. Stay tuned!

Startup Lessons Learned: Wear Your Brand Like A Billboard

Marc Cuban once said he’d never invest in a company that ‘wastes money’ on tchotchkes and promo stuff to give away to your customers. We don’t necessarily agree since the likes of Mailchimp has done a great job of branding through their awesome swag as well as their cool email marketing product.

At Dasheroo we’re not spending big money on branding things like watches or boxer shorts, we do use Sticker Mule for our cool (and cheap!) Dasheroo stickers and our co-founder & VP Customer Success actually made it a family project to silk screen some sharp-looking Dasheroo T’s for the team.

I consider it a smart, and high ROI, investment much more than just throwing swag at employees and customers. It’s advertising, and I wear it like a billboard. You can often find me just about anywhere I am sporting a Dasheroo T, and if not that I always have my iPhone with a Dasheroo sticker emblazoned on the back cover.Dasheroo branding

I get so many people that may not have struck up a conversation before, asking me “So what’s Dasheroo?” And since everyone business in the world needs a dashboard, I’m confident my explanation will be relevant to the person next to me.

So when I pick up my phone, point at it while I give the elevator pitch about Dasheroo, a few things happen:

  1. People are instantly drawn to the colorful logo and (they say) cute name; they smile and want to know more about what Dasheroo does! Nice branding opportunity!
  2. They see me smiling because I love what I do.
  3. 9 outta 10 times they ask for a business card (which is a fun square card with our logo and fun pictures of the Dasheroo sticker on the back, thanks Moo cards!)
  4. Often they ask for a job, or
  5. They are interested in a demo, a partnership or just launching right in and paying us. Recently, I even had a very interested person ask if he could buy us! (I factored in the 2 bourbons he had drank while we conversed into this;)

So bottom line, even though in SF and many other tech hubs large and small it seems like everyone is sporting swag of some sort, if you create cool branding and wear it well, you ‘ll get plenty of folks striking up conversations with you. And who knows where they might lead, but I guarantee you my ROI has been fantastic!