Sales Assembly’s Sales Souffle is a monthly collection of tips, trends, and tactics to help you navigate the Michelin Starred world of Tech Sales – featuring yours truly, Chef Matt Green, Chief Revenue Officer here at Sales Assembly.

Bon Appetit!

The grass isn’t always greener, folks.  It’s an admittedly clichéd term that bears repeating given two things:

  1. The hyper-competitive talent market right now for salespeople. If you’re an individual contributor with 6+ months of experience, I can only imagine the number of recruiters who are sliding into your LinkedIn DMs at the moment.
  2. The number of ICs who have joined a new organization only to slide into my DMs a few months later saying “Hey, this isn’t really working out.”

It’s easy – and completely natural – to be lured by the prospect of rapid career advancement, and promises of a higher OTE made even more attractive by the company’s coordinated LinkedIn posting blitzes that all contain way too many 🚀🚀🚀.

In addition to ensuring you have a passion for the product they sell, the amount of research you do on a potential employer should exceed the amount of research you do on a prospect before your first cold outreach by at least a factor of 100. Sure, look at platforms like Glassdoor and also count your blessings that RepVue exists, but be sure to go a few steps further.  Leverage LinkedIn to see the average tenure of folks who are in similar roles as you, and pay attention to what their advancement (if any) within the organization has looked like. Look at folks who used to work there, and don’t hesitate to shoot them a message asking for unfiltered feedback. Do some digging on the VP Sales and/or CRO. Read through posts they’ve made, listen to podcasts they’ve been interviewed on, etc – you get the point.

If you’re a halfway decent B2B software sales rep (which is, outside of my Dad, presumably the only people who consume this Souffle every month), the world is legitimately your oyster right now, and it will always be that way until the moment it isn’t.  If you’re considering making a move, do your darndest to ensure it’s the right one.


I first mentioned Scribe earlier this summer as one of the most, if not the most, impressive productivity and collaboration tools in recent history. Based on my plug-in this powerful newsletter that is read by titans of industry across the globe, they were just able to raise a massive $30M round!

If you haven’t used Scribe yet, you’re missing out big time.  Bonus points that it’s completely free to use!  They recently completed a revamp of their entire platform and now count a few decent brands (Amazon, Tesla, Visa, etc) as customers. I can’t stress enough how powerful this tool is for any team (sales, CS, operations, etc) that wants to spend less time explaining to others how to do stuff, and more time actually doing it.  Seriously – do yourself a favor and check it out!

Below are a few tips from leading B2B tech sales pros from across our awesome community:

Joey WilliamsSDR Growth Manager – Chili Piper

Q: What do you see most SDRs doing wrong?

A: Quantity vs. quality is a constant balance as an SDR, so I’ll answer this by providing an example from each where I see a lot of SDRs struggle. 

Quantity: A/B testing is extremely important as an SDR, but a lot of reps get caught up making judgments about the effectiveness of their outreach far too quickly.  The SDR role is always going to be over 90% failure, so if you are making snap judgments after sending ten emails and not getting responses, you’re missing the bigger picture.  When you come up with a new message you want to try, or a new line for cold-calling, you need to do it 100 times every day until you have significant data to compare.  You’d be surprised how many reps will try something 5-10 times and decide it doesn’t work for them.  “Mindset” as an SDR is extremely important and you have to believe that if you try something 200 times you’ll get at least some responses to influence your future messaging and drive results. 

Quality: I always tell our team that the instant someone sees an email or message from an SDR, their assumption is most likely “they’re reaching out to book a meeting because it’s their job and I’m one of their assigned prospects for the quarter.”  Still, a lot of SDR outreach includes lines like “I think it would be a great idea for us to meet” or “this would be a perfect fit for you” without earning any trust. 

If you consider that as a prospect’s first reaction, it makes outreach a bit more simple when you consider that you’re already handling an objection from the moment you start reaching out.  So, the question you need to answer the moment you start typing that first cold email is “why are you reaching out to me?”  Find a way to repeatedly and efficiently research your prospects so you can say what makes them a good fit for a meeting.

As someone receiving outreach from SDRs, I can’t tell you how refreshing it is when someone starts their email with a genuine reason (about me or about Chili Piper) that they think we’d be a good fit for their product (IE our team has grown X amount in the last quarter, we manage X number of SDRs, we have a specific piece of content on our website that shows our intentions in a certain area, etc). 

Again, quantity vs. quantity is always a difficult balance, but an SDRs role is to make sure they’re doing intentional outreach and enough of it to take luck out of the equation and set themselves up for results.

Michelle VuSenior Director of Sales – G2

Q: If I am having a slow month/quarter (we all have them), what steps should I take to keep motivated and move forward to get back on track?

A: I look at this in 3 ways, mindset, data, and collaboration:

  • Mindset, in my opinion, is the single biggest tool in your toolbox that only you can control. Understand where your head is in that moment and think back to the successes you have had.  I always recommend creating a ‘warm, fuzzy’ folder or a ME folder, putting all the achievements, nice emails from customers, co-workers, etc in one spot, and go to that for motivation.  You can and will get back there!
  • Data- as we all know, numbers play a huge part in our role.  What is your current win rate?  Based on that, how much pipeline do you need to create to get back on pace?  If you have a call recording tool, can you pull out themes from the closed won deals?  Set small goals week by week.
  • Collaboration- never lose alone, never win alone.  Crowdsource from your peers what’s working and never be afraid to try a new tactic.  It’s the beauty of sales, you never know what will get you a meeting or that next deal, we always have to be creative and evolve. 

Hi {first name}.  76 Percent of B2B Buyers now expect much more personalized attention from folks trying to sell them stuff. It’s imperative that you get a good understanding of who you’re selling to and specifically why they would need your solution prior to reaching out.

Further to the above, 88% of B2B Buyers only make a purchase when they see their sales rep as a “Trusted Advisor.” Lead with value, offer impartial advice, and leverage your inner Todd Caponi by embracing transparency throughout your sales process.