Sales Assembly

Elevated Learning & Development for GTM Teams.

Sales Assembly's all-inclusive annual membership for the entire GTM organization combines strategic skill development, robust peer communities and an easy-to-use learning platform.

Co-Founder and Chief Revenue Officer

Pavilion

Chapter Head

VentureOn Partners

General Partner

Sandalphon Capital

Sandalphon invests at Pre-Seed and Seed stages in B2B and Consumer startups across the Midwest as a lead, co-lead or meaningful investor.

Portfolio Advisor

RepVue

With RepVue, sales professionals can immediately know what it's like to sell for any of the world's most well known sales orgs. Detailed compensation and quota attainment data, culture scores, product market fit scores, diversity and inclusion scores, and much more. Rate a sales organization at repvue.com to join. It's anonymous and takes just a couple minutes.

Investor

Amper Technologies

Amper enables manufacturers to always meet production targets and level-up operations using real-time visibility. With our powerful machine monitoring and analytics tools, teams can easily identify the root causes of issues and systematically unlock hidden capacity and production losses. Born on the shop floor, Amper is simple to use and takes only minutes to deploy on any kind of machine. We empower entire manufacturing teams - from operators to plant managers - with actionable data and intuitive software. Amper's vision is to create a FactoryOS to unleash the potential of every manufacturer and create world-class operations.

Amper is headquartered in Chicago - check us out at http://amper.xyz/

VentureSCALE

Powered by Sales Assembly, VentureSCALE is the first & only Growth Accelerator for early-stage, venture backed B2B technology companies. Our program helps companies to learn about, develop and implement the most important aspects pertaining to sales...resulting in the foundation for scalable, sustainable and predictable revenue growth. 
​
Applications for the 2019 cohort close on 9/16/19

Co-Founder

Techstars

Techstars helps entrepreneurs succeed. Through the Techstars Worldwide Entrepreneur Network, founders and their teams connect with other entrepreneurs, experts, mentors, alumni, investors, community leaders, and corporate partners who will help their companies grow.

Mentor

The Chicago Leadership Alliance

The Chicago Leadership Alliance (CLA) provides a community for Chicago’s most ambitious, benevolent and well-connected young leaders. The CLA offers members an opportunity to interact and build important relationships, while also providing members with the forum to leverage collective influence, resources, experiences, contacts, ideas and fresh perspectives...all in order to benefit others, and accomplish otherwise unobtainable objectives. The success of The CLA stems from our simple, yet powerful and inspiring Action Statement: “Collaborating for the betterment of others, our city, and our members.” Through organized leadership and structure, there are four main components that drive The CLA: Philanthropy, Civic, Business, and Social.

Member Board Of Directors

Holiday Heroes Foundation

Board Director

CRO of Sales Assembly | Investor | Portfolio Advisor | Decent Husband, Better Father

I've led sales and operations for multiple hyper-growth, venture backed tech companies.  In these roles, I oversaw personnel management, strategic planning and sales leadership in multiple markets across the U.S.  I now help run the first and only Scale-as-a-Service platform for the country's most exciting B2B tech companies.

Earlier in my career, I served in leadership roles in both Fortune level and boutique investment banks where I led business development teams and served as Interim Head of Sales for multiple portfolio companies.
 
I'm also a pretty good husband, an even better father, an international travel enthusiast, and if there's a Simpson's quoting competition I would undoubtedly place in the top 3 (provided the focus was on seasons 1 through 11).

What happened the last time I answered a call from an unknown number? 

I don’t know because I haven’t done that in years other than by accident when my finger slipped, and I found myself on the phone with someone selling a time-share in the Bahamas. 🤨 I imagine other people may feel the same. 

Yet B2B revenue leaders are still encouraging reps to make 100+ cold calls a month, thinking volume is everything. 

Most people just don’t want to be reached that way anymore - it’s not a good use of your team’s time. 80% of cold calls go to voicemail, 90% of those voicemails are never returned. 

Try putting more effort into less outreach.  Try sending a personalized note.

If you wanna separate yourself from the noise, then actually separate yourself from the noise. 

Cut your target list in half, narrow that half down to the most qualified, and research....

Every. 
Single.
Prospect. 

Not saying calls don't have their place, but IMO effort and thoughtfulness are what matters most these days. 

Matt Green

Our first of at least 10 dinners this year across the country for VP and C-level revenue execs kicked off last night in Chicago and, holy moly, we were close to standing room only!

This one was special, and not because we had 37 people in the room…

July will mark 7 years that Sales Assembly has been around, and many of the leaders - and their companies - in the room last night have been with us since then.

Without their support early on, there is no Sales Assembly.  

The amount of trust these leaders have been placing in us isn’t something we take lightly.  

We train their XDRs, AEs, CSMs, and AMs every week.

We provide leadership development for their aspiring managers.  

It meant a lot when Todd Caponi was client number 1 back in 2017.  

It means alot that a handful of companies in this room recently signed multi-year renewals to keep our relationship going into the 9th (!!!) year.


Anyway, as with all of these dinners, the human to human stuff is the best part:


- Hearing about Maggie’s new drag racing hobby on the weekends

- Realizing Jessica and I just happen to be planning on spending the Xmas holidays in the same area

(and watching her buy one of Todd’s books off Amazon right on the spot)!

- Seeing Eric working the room and busting peoples chops about their G2  profiles

- Watching Kyle Asay realize that Jen stood him up for their first IRL meeting


Also lol at me convincing Ross Rich  and 💜 Will Allred to fly in for this by telling them I was taking them to a Bruno Mars concert.  

Suckers.


Finally, thanks to our longtime bffs at IDA Ireland along with the AMAZING newly launched TigerEye for their partnership in making last night possible!

Next up: NYC on 4/4.  Scott, I’m bringing a contract for you to sign. 😡

We make some pretty epic mistakes in sales.

Back in my previous life, I had the chance to do some work with a guy who was one of the chief fundraisers for Obama's 2008 campaign. 

He was a relatively young dude, but extremely successful.

Over coffee one day, he said something that has always stuck with me:

"Much of my success comes from having friends in low places."

If you're not singing a Garth Brooks song right now, you're hopefully thinking:

"How often do I spend time proactively developing relationships with the people in my deals that have very little decision making power, but are still important parts of my buying process?"

Relationships matter, but more importantly, EVERY relationship matters.

NYC always has great energy.  That energy is compounded whenever you gather 28 revenue leaders into a room!

Sales Assembly was back in the Big Apple last night, at my favorite venue in the city - Quality Meats - hosting the 2nd of at least 10 dinners across the country this year.

Because it was an event for SaaS sales nerds, 💜 Will Allred obviously busted into the room like the Kool-Aid Man and made an appearance.

We also had the opportunity to toast Victoria’s new podcast, while she made clear she would never consider me as a guest. 🥺

Mark busted out a cardboard box and challenged Adam to a breakdancing battle.

Had the chance to hear the latest and greatest about Drew’s and Jonah’s families.

Ang and I, as two introverts, strategized on how we could each find a way to leave as early as possible, since spending 3-4 hours in a crowded room is 🙅‍♂️ for folks like us.

And, sure, we talked a bit about referral marketing, deal acceleration, ABM, etc etc.

I was mainly here for Mark's airflares and Adam's head spins!

Thanks as always to our great friends at Capchase and Reveal for making such an amazing evening possible.

It’s not every day you get to turn a vision into a reality. 

Super excited to share that Delilah Singer & I have our OWN podcast, “Huddle Up” now featured on LavenderLand!

Episodes will include anything and everything about SDRing, navigating the tech world, personal stories, & of course, awesome guests.

HUGE thank you to 💜 Will Allred, William Ballance, Chelsea Castle, & Todd Clouser for giving us the platform to share! 

Can’t wait to continue to partner together 💜✨

Check out first episode here: https://lnkd.in/eFfzJU_R

#HuddleUp #SalesDevelopment #SDR #LavenderLand #WomenInTech #LivePerson #LavPerson

If you're a sales rep and heading to an industry conference, be sure to connect with your CS team and get a list of current customers who are ghosting them.

Cross-reference that list with the event attendees.

Dedicate a few minutes to seeking them out and striking up conversations.


Will they be the POCs your CS team has been trying to get in touch with?  Likely not.

But after schmoozing them for a bit, I'm sure that -if you ask nicely - they wouldn't mind making sure the POC sends a standard:  "Sorry, been heads down over here..." apology email to your CSM and finally books some time.


You (or someone else on your team) worked hard to close em.  

Might as well invest a few minutes ensuring you're in a good spot to keep em.

If you’re chasing a love interest, and you text them multiple times over the course of a month but don’t get a response, it’s generally not a good thing (in my experience). Same thing in sales - 

When a prospect ignores your outreach for over a month - especially if you’ve already done the demo - they’re probably not interested.

Do your due diligence, it can take a number of follow ups - but after a month or two, the spark usually fizzles. 

And you have to accept it.

Part of what drives the deal is hype, attention and communication. The longer time passes without momentum, the less your prospects remain engaged and invested in the opportunity.

Could you reach out next year? 

Definitely, with enough time, conditions change. 

They may have new perspective, maybe their budget increased or needs changed…maybe they dated someone who wasn’t as funny as you and realized their mistake!

But for now - leave it be. 

Spend some time gathering more qualified leads, and let this one go. 

Averaging a bit over a new logo per week so far this year.  There are 2 tools that fly under the radar right now that have helped me, the only full-time seller here (and a terrible one at that) make this happen: Fluint and Deeto:


For a bit of context, we're a mid-markety kind of sale.  Usually between 2 - 5 stakeholders.  

Leveraging these 2 tools has cut the number of calls I've needed to hold in half, and shortened the sales cycle dramatically.


Fluint:  Any non-transactional salesperson that isn't using this is missing the boat.  Big time.

Take your call recording.  Immediately turn it into a clear, concise, single-page business case using the buyers language.  

The kind of thing that check-writers actually want to read when your champion brings them something for approval. 

I dont think I need to say much more than that. 


Deeto:  Most users leverage this platform to manage their customer references and make it easier for their prospects to book reference calls in later stages of the sales cycle.

I say to hell with waiting until late in the sales cycle.

I don't wait until later in the sales cycle.  I don't wait for prospects to ask me for references.  

I send them to the Deeto platform after the first call (provided my feels are that they have legitimate interest as a prospect).

I LEAD with my references.  After all....why not?

"Before we reconnect next week, feel free to book some time with another VP Sales or CRO who has been a member of Sales Assembly and get some unfiltered feedback."

The reality is that they very rarely do book a reference call that early.  The beauty is that they don't really need to.

After logging into the platform, they see names of 10, 20, 30, 40+ people they might recognize, leading revenue for logos they're familiar with, and are able to peruse customer stories and testimonials at their leisure.

All of them WILLING to hop on a reference call at the click of a button.

That's usually all the validation they need.


If they do end up deciding on a reference call, well, that's why I keep sending Keith gallons of ice cream every quarter.  

As long as the positive feedback keeps flowing, I keep his blood sugar nice and high. 🤝


Anyway, there are a lot of tools out there to evaluate.  They all promise great things on the sales side of the house.

A good amount of them actually deliver on those promises.

Fluint and Deeto most definitely do.  


Chicago folks: longtime Sales Assembly member 1WorldSync is looking for a Director of Sales to lead their SMB team.

You'd oversee a team of both AEs and AMs.

You'd get to work alongside amazing leaders like Kathleen Lord and TJ Waldorf.

They've been a Sales Assembly member for 4 years, meaning they believe in making investments in the personal and professional development of their teams. 🕺


Seems like an amazing opportunity.  JD down below. ⬇️

I never thought about using an on-site mtg with a prospect as a great way to qualify the health of an opp.  Lucky for me, I'm fortunate enough to be able to hobnob with leaders like Dan every day.  He brought this idea to the table last week...

Sales reps, if your deal is progressing towards the finish line, position on-site meetings with C-level executives as a must-have.


If a mix of stakeholders aren't willing to get together and meet with you, that speaks volumes.

In essence, the physical meetup is a chance to gauge genuine interested amongst all players involved, especially the elusive execs. 

The time commitment and coordination required acts as an implicit qualification. 

If core sponsors decline or send delegates instead, you can reasonably deduce that prioritization levels might not be as strong as you hoped.


Will an in-person visit seal every deal?  Nope.

Will deals close WITHOUT an in-person visit?  Yup.


That said, this is a great way to truly qualify deal health.


Bonus: I can guarantee you that your competitors are likely not floating the idea of in-person meetings.

Get that face time!

Any kid who’s sold something door-to-door knows one thing: pitch the big houses first. 

That’s because they’ve intuitively identified a key element of GTM strategy - customer segmentation. 

You have to prioritize accounts with the highest value and opportunities. People with money to spend on your product, an interest in what you’re doing, obvious use cases, and/or who live in mansions.

Speed and efficiency are critical when you enter a new territory because you only have a limited window to make an impact, and your budget tends to go quickly. 

Strategic customer segmentation informs your positioning, and shows your sales and marketing teams where to focus outreach.

Identify which clients have the highest lifetime value, and potential to generate the most revenue. 

Look at those who are similar in your existing customer base and note any key traits, behaviors or interests. 

Target the people worth targeting. 

Otherwise, you’re going to be out in the heat sweating while your chocolate bars melt.

It's important for sellers to focus less on what their champions are saying, and more on what their champions are doing.  Especially when forecasting. 

As someone who has the happiest of happy ears, I've made it a point to intentionally become much more cynical in my old age.


- Are my champions actually sending my business case around to other stakeholders? 

You can easily track this activity via platforms like Accord, or simply look at how many times your email has been opened in Hubspot and infer from there.


- Are new executives being added to follow-up meetings?

Even if I'm talking to the decision maker, buying is almost always done by consensus these days.  

We sell primarily into VPs Sales / CROs and Enablement leaders.  I'm not feeling comfortable about the sale until I meet the VP of CS and/or Account Management as well.


- Am I getting questions about SSO and other technical capabilities?

Pretty self-explanatory there.


Anyway, by embedding key behavior tracking into opportunity qualification, we gain objective clarity into progress towards critical milestone events that signal real transformation ahead.

That's basically thesaurus talk for:

"The deal is actually taking steps forward and worth moving into the next stage of your pipeline."

Gone are the days where you could charm your way to a good deal with the right buyer (at least I’ve heard of people doing that)... 

Now, it takes an average of 5 decision-makers in every sales process to close a deal - that’s the average. Sometimes, more like 20+.

What does that mean for the sellers?

It’s going to take awhile, and you need to cast a smaller net to maintain focus. 

Every “buyer” includes stakeholders in different departments - could be a lawyer, operations manager, the CFO, the CEO, even a department manager. 

You need to do your due diligence on all those people, and see out internal champions who can put in a good word. 

It's not just about pitching a product; it's about navigating a complex web of relationships and interests. 

You need to get in with the dad, mom, uncle, best friend AND dog if you want to get that sig. 

Optimism does not = a reliable forecast.

Overconfidence prompts businesses to make bad decisions with costly consequences (same thing at the race track). 

But there are ways to avoid letting positivity lead you down the wrong path.

Try a “pre-mortem” 

It’s a way to anticipate potential calamities as a group. Rather than wait to look back at all the mistakes that were made (i.e. post-mortem), consider problems ahead of time and imagine how they roll out. 

Here’s a good exercise:

- Get with your team, look 12 months down the road, and envision your project turning into a disaster

- Ask each team member to spend a few minutes mapping out whatever disaster they see unfolding

- Share notes 

- Point fingers 

- Reconsider the plan

This technique keeps your ego in check, avoids group consensus, and provides for a more objective and realistic analysis of the bet you're about to make. 

If the risk proves minimal, go ahead and roll the dice.

It’s good to be proud and confident in your business. 

But it's no bueno to believe you’re infallible.

How many meetings on your calendar are seemingly unnecessary?  Probably quite a few, and here’s why -

A) Someone thought you should “check in” even though there’s nothing to discuss.  

B) Some exec doesn’t know the answer to a question and pulls X number of people into a room, where little is accomplished. 


Managers surveyed by Harvard Business Review said they believed 83% of meetings on their calendar were pointless. 

It happens internally a lot, but even externally when you feel the need to touch base with a client. 


Here’s my way around it - 

1 - Every year, I do the thing where you delete all your recurring meetings and start over - add only what comes up and feels necessary. It works.

2 - Only include people in meetings that need to be there - and be intentional about it. If it means literally asking someone, “Do you know anything about X, Y, and Z?...” do it. 

3 - If you’re just trying to get face time - which is important! - make sure you go into it with a goal in mind. Even your 1:1s. Pick a project to focus on, use it for feedback, discuss a challenge or problem you can collectively solve.


Above all else - have an objective in mind and the right people to accomplish it. 

As a new quarter gets into full swing…this is a good reminder. 

How many companies have 70% or more of the sales team attaining quota? 

Not 50… Not 100… Not even dare I say 150… 

It’s 200+ companies 

These are companies that are doing it right. 

Their culture, leadership, PMF, etc, but most importantly… this all leads to a company’s ability to put the team in a position to hit quota. 

See the full list: https://lnkd.in/g9F4DFrU

#repvuepartner

Your colleague asks for assistance on a project. You’re booked back-to-back, but feel obligated to support them. What do you do?

If you’re like me (ie terrible), you tell them you’ll help in a week or two. 

That's a mistake.

Here’s why:

By committing to provide work on a later date, you’re devaluing your time in the future. The odds are, if you’re busy now, you’ll be busy then.

A better rule of thumb: Base your calendar down the road on your calendar now, and act accordingly.

Time has value, just as much as money.

Start time tracking. Specifically look at how you’re allocating the hours of your day.

Not just “I’m at work,” but what you’re actually doing.

In my case, there are 2 hours allocated every day to sourcing stupid memes to use as comments on Keith’s posts, but I digress...


Take note of what’s most valuable. If someone asks you for time and help today, be honest, let them know about your priorities, and don’t overcommit.

You can even say, “I may be able to help in six weeks, but given how much my schedule fills up, there's a good chance I won't be able to get to this then either."


It's not only about protecting YOUR calendar, but more importantly, it's about being honest with people that are relying on you.

If you can't realistically commit to it, then don't do it, and instead try and help your peeps find the support they need elsewhere.

Sellers, if you're looking for a way to qualify the health of your deals, here are 5 simple questions to ask yourself before walking into your next forecasting mtg:


1) Is my prospect willing to co-invest time & resources?

Have they helped you put together an internal pitch deck or business case?  If the only time they are allocating is hopping on occasional calls to exchange pleasantries with you, be wary...


2) Does my prospect reference our solution to others internally?

A question I ask whenever I meet a new stakeholder:

"Just so I don't bore you with stuff you might already know, what has [champion's name] told you about Sales Assembly?"

If their response is "I had this invite in my calendar so I showed up," then you might have a bit more work to do. 😬


3) Can my prospect cite a specific use case they'd tackle first?

Vague problem statements = low urgency.  

"We just wrapped up Q2 QBRs. A big topic on the agenda was enablement and raising the IQ of our Strategic sellers. Sales Assembly is a key part of the equation."

The above is cut and pasted from an email from a new logo we added last week.  

That's along the lines of what you're looking for.


4) Has my prospect given me clear next steps?

Self-explanatory.  "Reach back out in a month" isn't really a clear next step, btw.


5) Would my champion be surprised to know I'm forecasting this deal?

My personal favorite.  Answer this honestly.  If you're unsure, don't be afraid to ask your champion directly:

"It seems like we're on track to have this done by end-of-month.  Do you feel the same way?" is a simple version.


As someone who has the happiest set of happy ears in existence, level-setting on all of my deals via these questions has helped me a ton.


Want to nail your demo? Do what Sam Altman just did on Twitter...

To hype OpenAI’s new product Sora - an AI text-to-video tool - he posted a tweet asking for people to send him captions of images they wanted to create. A few minutes later, he shared the results on his feed…

The pics were both fantastic and bizarre (dogs podcasting…whales on bikes…weird stuff) + they generated a lot of buzz. 

Not only did this bring attention to Sora (7 million+ impressions on the post), it proved the value and capabilities of the platform. Assuming these weren’t planted tweets, all images were made off the whim of the replies.

No cheesy promo videos. No pre-approved materials or staged results. 

Just a real time demonstration of what can be achieved. 

That’s how you wow with a demo. 

Get the client engaged with your product, let them test out their own needs and use cases. 

Involve them in the process. 

Mixed signals are everywhere right now.  

Some teams are growing and hitting goals, some are still falling short.

Some teams are hiring again for crucial roles, others are still going through layoffs.  

Regardless of your situation, this report by QuotaPath, in conjunction with our partner Pavilion, is super enlightening. 

Why reps are missing quotas:

Market Conditions ~37% - Clearly we aren't in the frothy ZIRP spend, spend, spend era any longer.  But we also aren't in the depths of despair any longer either (from what I see/hear).  The markets have shifted and if you haven't adapted by realigning goals and focusing on a defined ICP, then I dont know what to tell you.  My hunch is this answer is the catchall for "other."

Lack of experience or skill ~37% - This could tie into the first answer in that your reps had the skills to sell in an up market.  What they are lacking is true sales process and rigor to be able to swim upstream.  The biggest cure here?  Training & Enablement.

Misaligned sales activities ~36% - They aren't doing what they should be doing to progress deals in the sales process.  This is a leadership + training issue.  If your process isnt clearly defined with detailed next steps, then your reps are just spinning their wheels.  The first step is defining these activities, the next is tracking to ensure your reps are deploying them.

Poor time management ~34% - Blame it on WFH, blame it on wearing multiple hats, whatever it is, this has always been an issue.  Help your team focus on what's important and either outsource or eliminate the activities that are not.

New hire ramp-up periods ~33% - This has always been an issue but is probably more of a glaring one now.  With less enablement resources + hybrid work environments, its hard for teams to ramp their new reps quickly.  Chalk another one up to Training & Enablement.

Unstructured sales process ~33% - The sibling of misaligned sales activities.  If you dont have a defined sales process, you simply can't guarantee the right activities are being done.  Pick a sales process, any sales process, and stick to it.  Consistency is more important than worrying about if MEDDPICC is better for your org than Challenger.  Another Training & Enablement issue.

Lack of motivation ~33% - It's been a long few years.  Finding ways to drive excitement is half the battle right now.  Team building, surprise & delight moments, and investing in your people can all move the needle here.

Unrealistic quota or sales goals ~32% - This is unfortunately tied to the growth at all costs mentality.  Find a way to set realistic targets at the board level, then deploy books that are filled with high propensity to buy accounts directly in your target ICP, is one of the only ways to rectify this.  

*So if you are scoring at home, Training and Enablement is the biggest thing you can do to address many of these issues.  Process is the next biggest solution (also ties to T&E). 


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