Building Habits That Strengthen Discipline and Results

by Scott

One trait I correlate strongly with accomplishment is discipline.

When I look at people who are really at the top of the game, most of them are very disciplined about certain things within the domain which they achieve.

I’ve been thinking a lot about leveling up my own sense of discipline lately and wanted to share a few things I’ve found helpful in cultivating and maintaining this virtue.

Start With An Anchor

I think one thing that really helps is to have a discipline anchor early in the day. By anchor, I mean something you can count on to consistently experience a victory and check the first box to signal to yourself that you’re the one running your day.

Most days my anchor is a workout. I …
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15 Ways to Improve Software Demos

by Scott

Nothing is worse than a bad demo…

Even with a great product, a poorly executed sales demo can leave a permanent sour taste in your mouth about that company… and lots of aimless social media activity in the process.

My buddy Poya Osgouei who is a National Sales Manager at HackerRank put together a stacked list of best practices when it comes to preforming top notch Software demos.

Whether you’re a rookie or someone who wants a simple checklist, these 15 tips for improving demos serve as a great guide to make sure you’re dialed in. Enter Poya…


From leading and managing enterprise software sales teams at companies like Oracle and now HackerRank, I’ve learned a lot of lessons about what makes a strong demo.

Below are 15 suggestions that …
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How to Automate Personalized Email Outreach Without Breaking The Bank

by Scott

One of the big innovations in sales and marketing has been making personalized email outreach more efficient.

Today my buddy Nat Eliason from shares a completely free way to do this in the context of content marketing which he has absolutely crushed as SumoMe.

Many of the tools that I love like Salesloft, Outreach, and Tout cost $$ which mean they aren’t necessarily a great fit for someone who isn’t a full time sales development rep.

This alternative strategy for personalized email outreach Nat shares is awesome for making those one-off cold email instances more efficient when investing in a heavier solution like the ones above doesn’t make as much sense.

Enter Nat Dude…

The SumoMe blog has grown from 12,852 views last July, to 163,260 views this February. …
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Practicing Pre-mortems

by Scott

Before working on Troops, I was usually pretty good about reflecting on experiences after the fact…doing a “post-mortem” if you will.

Something I was less diligent about was this concept of “pre-mortems.” 

A pre-mortem means taking the time to map out what you expect to happen and the implications of that outcome. It sounds basic, but bringing process to this really makes a difference vs. haphazardly doing it here and there.

Consistently practicing simple pre-mortems at Troops has saved our team weeks worth of time by helping us realize that what we were about to do was not actually an effective use of time. I credit my colleague Aditya Pandyaram for instilling this process into our company and my life.

When you distill it down, trying new things are …
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Constraints As Your Advantage

by Scott

One of the biggest concepts I’ve become more self-aware of this past year is constraints and their effect on your speed and mental cycles.

Deep down a lot of people in early stage startups spend their time and energy thinking about “is this going to work?”

Even if you have a presumption of success for your company, at the tactical level you continuously ask yourself this question when evaluating everything from your business model to the adoption of a specific feature.

The best way I’ve found to holistically manage this circumstance is by implementing concrete, measurable constraints.

The magic constraint at Troops seems to be the number 30.

Do people want this product? Create a powerpoint deck and pitch 30 people.

How much should we charge? Pitch 30 qualified opportunities …
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Effective Cold Approaching and Follow Up At Conferences

by Scott

I was recently at Dreamforce, the largest enterprise software conference in the world. The goal was to connect with potential customers and future investors for Troops, as well as to get a better pulse on everything that is happening in the sales software ecosystem.

There’s a boatload of different tactics that can and should be employed at large conferences or events, and today I wanted to share two related to follow up and cold approaching busy people. 

Callback Humor

At conferences of this magnitude everyone is meeting a ton of people. Business cards are exchanged and sometimes you can meet 50 people in one day.

One challenge in these brief interactions is creating enough rapport that someone will want to hop on a call …
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Improving Influence and Persuasion by Developing “Writing EQ”

by Scott

Have you ever noticed that a smiley face at the end of the same exact sentence can completely change how someone interprets what you say?

Compare the following:

Let’s make sure this never happens again.

Let’s make sure this never happens again : )

In my experience something as simple as a smiley face can be the difference between coming off nice vs. appearing like a jerk.

Slight nuances in the syntax, punctuation, structure and semantics of your sentences can profoundly change the meaning and tone of anything you write. Any marketer or salesperson looking to persuade and influence should be acutely aware of this.

Below you’ll find a few examples where slight a variance in communication can influence how someone might interpret a statement:

Example 1: …
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Becoming High Performance and Building A Sales Machine

by Scott

Below you’ll find the first ever “guest re-post” on Life-LongLearner as well as a new podcast with my buddy Ryan Denehy. The post + podcast combo effectively  makes this a Denehy centerfold.

Ryan is a close friend who most recently co-founded Swarm Mobile which was acquired by Groupon. In the podcast episode, we riff on the mental and emotion journey of getting there. In the post, you’ll see all the things he learned building the local sales machine that fueled their growth.

Enter Sensai Denehy….

Listen On Itunes

“Building A Startup Sales Machine: 64 Things I Wish I Knew”

Newsflash: I had no idea what I was doing when I first started running sales and distribution teams almost 10 years ago. Some would argue that I still don’t. But the …
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