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The 3 Rs for Starting Sales Conversations

Earlier this year I came up with a simple framework for starting sales conversations, which we’ve used successfully as part of our target account prospecting initiatives. I thought I’d share and as always, comments and refinements are appreciated.

3 R’s for Starting Sales Conversations

1) Relationship (You know someone)
– They can book a meeting or make an intro for you
– You can name drop, use the relationship to get the attention of the person you want to get to

2) Recency (Recent Activity/Interaction)
-You met them (or someone from their org) at a tradeshow/event, or they were at least there

3) Relevance (Real Intelligence)
– You know they have a project
– There was recently something relevant in news that can be referenced
– There is something relevant in their LinkedIn profile that can be referenced

The “FIT” Assessment Framework

I was doing some thinking recently about how I assess members of my team, and what makes someone a fit. I came up with a framework that’s been working well for me as of late – both as I’ve reviewed existing team members, as well when I’ve interviewed for open positions on my team. Check it out, and let me know what you think.

The “FIT” Assessment

Character “FIT”
FIT from a character/personal perspective = F – Fortitude, I – Initiative, T – Talent
These are things that are more or less character/personal traits, and less about work output or specific contributions or performance.
Fortitude – Do they get rattled when things get tough? How do they perform under pressure? Do they have the strength of mind to execute and make the right decisions when things are difficult?
Initiative – Do they wait around waiting for you to tell them what to do? Do they come to you with ideas, and not just ideas – but fleshed out plans or the results of experiments/tests? Do they step up and take on more, and chose important, impactful things to jump into?
Talent – What are their innate talents? Are those talents particularly valuable to the team? Do they leverage their talents effectively?

Contribution FIT
FIT from a contribution/productivity perspective = F – Failures, I – Impact, T – Teamwork/Team Dynamics
Failures – What have the failed at? Have they had big, substantial failures? How have they responded to those failures? Do they “fail forward”?
Impact – What kind of impact have they had on the team? What kind of impact have they made on the organization? Are things noticeably different because of them? Would they be noticeably different without them?
Team Dynamics – How do they work with the rest of the team? Are they respected? Do they show respect? Do they drive others to do better, or do they drag people down? Are they setting an example?
I’d love to hear what you think.

The Hidden Gem in Your “Private Beta”

Lately, I’ve had the great pleasure of being able to work with startups from the Microsoft BizSpark program that are leveraging SaaSGrid to bring their SaaS apps to market. It’s really been a blast, and it’s great to see the success they’re having and the enthusiasm about our product and what it’s doing for their business.

One of the topics that has come up lately in discussions has been the concept of a “Private Beta”. Having been responsible for the go to market strategies and successful launches of software products in the past, I’ve been fortunate to have learned a number of things along the way. One hidden gem that I think many times is overlooked during a software company’s private beta phase is:

Gaining an understanding of the SPECIFIC thought process of how users evaluate the product.

Everyone wants users to tell them how great their product is and what could improve. But what if rather than just going to market with a slightly better product, you could also go to market with a keen awareness of how your target market will be evaluating your offering? This isn’t the easiest thing to do, and in order to do it, your private beta needs to be structured with this objective in mind. It can’t just be “use it and tell us what you think”. You should have a set timeline for the private beta, with well defined milestones and feedback loops, just like any other project.

Here are 3 major things to consider that should help you on your way:

1) You want to understand what the private beta users expectations are going in, before you provide them with access. You want to understand what they hope your product will do for them, what they think it will do for them (based on your website, the information you’ve given them in the past, etc), and why they are interested.

2) Next, you want to understand their immediate first impression. When they initially are provided access, what did they think? What questions did they have immediately? What impressed them right away.

3) Further on, you want to understand the reasons that these users find value in the offering
Capture this information, document it, analyze it…etc.

Ultimately, you want to understand what you can do to keep your future customers engaged and extremely successful at every point of their relationship with you. When they initially contact you, when they are evaluating your solution, when they sign on and begin using your product, AND hopefully when they are evangelizing your product to others.


Here’s an example of a first step and email to kick things off:

Send a precursor email or call (depending on your participant numbers) that tells them that you are preparing to open up access to them in the coming week, but that first you would like them to tell you why they are interested and what they hope your product will do for them. Ask them to simply respond, so that you have some real data about their personal expectations and hopes for your product.


Hello _______,
Thank you again for your interest in <INSERT YOUR PRODUCT NAME HERE>.
We are excited to inform you that next week we will be providing you access to <INSERT YOUR PRODUCT NAME HERE> in response to your interest in our Private Beta. Before that time we would like you to simply respond to this email and tell us why you are interested in particpating, and what you hope <INSERT YOUR PRODUCT NAME HERE> will do for you. We are collecting this data now, before you see <INSERT YOUR PRODUCT NAME HERE>, so that we have an understanding of what your personal expectations and hopes for our product are.
Our goal is to make our customers/users wildly successful. Understanding your expectations prior to your initial impressions will help us to better hone our messaging, so that we can communicate the value of our offering most effectively.

We greatly appreciate you taking the time to respond with this information and we look forward to working with you.

Event in NYC Tomorrow and Webinar on Friday

We have a few events coming up this week at Apprenda, and I thought many of you might be interested:

Going From SaaS Product Idea to Paying Customers in Under 6 Months (WEBINAR)

When: September 25th, 2009 at 1:00PM EDT

This will be a great event. You’ll have an opportunity to hear from Nate Rowe, CEO of Appoint IT, who recently launched their product offering, and was able to go from a product idea to paying SaaS customers in under 6 months by leveraging the SaaSGrid SaaS Application Server.

You’ll also get a chance to hear from Luis Aburto, CEO of Scio Consulting, and myself. It will be a great discussion, and you’ll see why SaaSGrid is quickly becoming the solution of choice for ISVs large and small as they make the move to SaaS.

You can find out more details about the event, and register

“How to Fail Miserably as a Cloud Software Provider” (NETWORKING EVENT)

When: September 22th, 2009 at 6:00PM EDT
Where: Public House, New York City (Lex/3rd)

This will also be a great event, and an opportunity to network with some movers and shakers in the SaaS and Cloud Computing space here in New York. You’ll also have an opportunity to hear from Apprenda CEO Sinclair Schuller, and he’ll be delivering a presentation entitled: How to Fail Miserably as a Cloud Software Provider”. If you’re in the area or can be, you won’t want to miss it!

You can find out more and let us know you’re coming here. We hope many of you can join us!

– Jesse

Great Presentation for Software Entreprenuers and Startups

Here’s a great slideshow I came across by 16 Ventures, from a recent seminar they held in Anchorage, AK. Great stuff, and real crisp and to the point. Having worked at a few software startups in the past and now interacting with lots of established software companies and startups at Apprenda, I would definately recommed you check it out if you’re thinking about launching a new software venture. They’re also holding another seminar next week on Feb 26th in Dallas, TX.

Start Smart: Positioning Your Software Venture for Success (2 hour version)

SaaSGrid is Amazing

Sorry for the LONG period of inactivity. Things have been extremly busy here at Apprenda. We launched SaaSGrid for general availability back in the begining of December, and the response has been phenominal.

Let me try and explain to you in a nutshell what SaaSGrid is, and why it’s game changing:

SaaSGrid is a true cloud operating system. It’s not a software application, with some plugins. It’s not a virtualization technology. It’s not a full closed stack cloud offering. (Apprenda does not host SaaSGrid)
It’s not like anything else on the market today.

SaaSGrid is the real deal. It is a truly groundbreaking technology offering that allows companies to move their existing .NET based applications to a pure SaaS model, or build new SaaS applications without having to expend any effort on the SaaS specific architecture (ie: multitenancy, scalability, etc) OR the SaaS specific business components that they need to run THEIR business. (ie: billing, metering, provisioning, etc).

Much like the desktop operating system catalyzed a new era of software innovation, SaaSGrid is doing the same thing. By providing a new layer of abstraction that contains all of the mission critical “SaaS DNA” so to speak, software companies can once again focus on writing great software and not having to worry about the intricacies of the delivery method.

If you are an existing .NET ISV, or someone looking to develop a new SaaS offering with any of the .NET languages, you absolutely owe it to yourself to check out SaaSGrid.

Thank You Autotask

Starting tomorrow, November 6th, I will no longer be Autotask’s Community Evangelist. I’m extremely excited to be joining Apprenda as Director of Business Development. The work that Apprenda is doing is game changing, and there is no place I’d rather be at this point in my career.

I’ve been with Autotask for 2.5 years now, and it’s been an awesome ride.

Just over a year ago we launched the Autotask CommunITy, which originated as a “skunkworks” project of mine. From the initial idea, to its conception and continued improvement, the Autotask CommunITy has been my full time responsibility at Autotask for the last year. In that time, it has grown incredibly into a thriving community of over 13,000 members and has radically impacted the way Autotask as a company operates. To cap it off, last night we were awarded a coveted ITSMA Marketing Excellence Award, specifically for the work we’ve done with the Autotask CommunITy. That honor is just as much the claim of the thousands of brilliant IT professionals that make up the Autotask CommunITy, as it is any of ours.

In addition to the Autotask CommunITy, I was also able to help Autotask launch its product on the global market back in 2006 (my first project). Then in early 2007, I was able to help introduce Autotask’s first mobile solution (Autotask LiveMobile). I’m extremely thankful for the work I’ve been able to do with Autotask over the course of the last 2.5 years. It’s been challenging, fulfilling and rewarding. As their 65th employee back in 2006, they’ve now grown to over 130 people, and last week were awarded the New York Capital Region’s Best Places To Work award for the 5th straight year! No other company has ever received the award so many years in a row, and it’s really a testament to the great people that I’ve had the pleasure of working with there for the past 2.5 years.

I want to thank all of my co-workers at Autotask, and all of the members of the Autotask CommunITy for such a wonderful experience. I could name names and go on for pages thanking individuals, but I’ve made it a point to personally speak with many of you already.

Thank you all, and best wishes for continued success.

Freshbooks Announces Quarterly Industry Benchmarks

Today Freshbooks announced that they will be publishing aggregate benchmark data on a quarterly basis. They’ve been sending out this data and more to customers for some time now, but now they’re going to publish some of the data to the general public.

Check it out, and if you are a SaaS company, take note and learn from these guys. They get it, and they continue to come up with creative ways to leverage the delivery method.

Great product, great company, great service. I can’t say enough about these guys!

Here are a few additional posts of mine about Freshbooks:

Freshbooks – SaaS Through and Through

Freshbooks = Awesome

Interview with Dean Isaji of ThinkMentalModels

As someone who’s always been fascinated by the human mind and how we think and make decisions, I was very interested in the concept of multiple mental models, outlined by Charles Munger in Poor Charlie’s Almanac. Back in May, I was introduced to, and conversed with Dean Isaji, author of the ThinkMentalModels compilation.

I recently had a chance to catch up with Dean and I ask him a few questions about the multiple mental models concept, and his work.

Dean’s Background

A bit of a background on Dean before we jump into the questions. Dean is a graduate from Cambridge, England and first worked in South Africa, for Eskom (the utility company). After completing his MBA at the University of Cape Town and then, after a spell in Hong Kong, he began working in the strategy and planning department at British Airways, in London. Presently Dean is pursuing some entrepreneurial ventures in America, through his own holding company.


1) How long have you been interested in the concept of multiple mental models?
I have been reading and thinking about the mental model concept for about 9 years. In the main this has consisted of reading – a lot – and making copious notes. The initial idea of trying to think better came from reading Tony Buzan’s Mind Map book.

2) What motivated you to compile the Think Mental Models collection?
At first, I wanted it for my own reference – thinking it would be handy to have it accessible on a PDA via the internet. But after reviewing the initial idea with some friends, I thought there would be real value to others. Hence I have complied an affordable PDF available for purchase.

3) Of the 130+ models contained in the collection, are there 10 or so that you find are used the most?
The most used is the ‘disconfirming evidence’ model. I have then broken the others up into various categories – more specialized than the broader website categories – and use a memory system in order to apply them to a given issue. I cannot really say that there are therefore 10 most useful models.

4) What is the greatest benefit that you have reaped from using the multiple mental models approach to decision making/problem solving?
I have found that I’m able to think with more speed and rigor when confronting an issue. There is the added advantage of ‘confidence’. This is a little harder to quantify, but – paraphrasing Charlie Munger – the confidence comes from almost always being able to provide useful inputs in a group setting, often with people much smarter than myself.

5) Do you have suggestions for study tactics and ways to retain the mental models outlined in the collection?
I do use an extensive memory system and I practice the models on a daily basis. At this point I don’t really want to get too much into execution as I may develop it into an online course.

6) Any additional suggestions or information you’d like to share.
What I have found surprising is that many people cannot immediately see the benefits of thinking broadly across disciplines. But even considering my own education, at no point was I taught to ‘think about how I think’. This is probably true for others and may be one of the explanations for why people tend to shy away from an active mental model process. The other reason may be much simpler. In ‘Men and Rubber’, by Harvey Firestone, the author recalls a Thomas Edison quote – “There is no expedient to which a man will not go to avoid the real labor of thinking“.

You can view a number of the mental models on Dean’s website. However, I HIGHLY recommend the ThinkMentalModels compilation PDF. At $4.45, it’s easily worth at least 10 times that.