Tyler Shedron’s Post

My basic #SoftwareSales trait.

Hopped on Insightly's account and gave my thoughts on what I like most about using Insightly + how our clients love the plug 'n play nature of the platform (while keeping technical horsepower). Really cool content idea by Courtney Duprey!

Social Proof is everything in 2024 & this current sales environment. Social Proof = being able to reference a current customer to a potential client that's similar size/scale, similar industry, and had similar challenges pre partnering with your company. In 2010s, potential buyers didn't have the level of access & network to evaluate products and services as they do now on their own. Because there was a lot of innovation and new tech entering the market, business cases to buy tech were are looped around over inflated ROI models given by software vendors using fake numbers. Buyers bought software with loft expectations of obtaining X in increased Revenue, didn't come close to achieving it, and spent a ton of money on the "Emperors New Clothes" (if you catch my drift on the reference). A terrible taste in their mouth. A major hesitancy to make future big commitments to software relationships. And any change management feels like a nightmarish thought. If you're not centralizing your outbound efforts on talking about your customers, if you're not talking drawing correlations to your happy customers during sales process - everything feels "Upstream without a paddle" (let me know if you're tired of my buzz phrases). More than ever, buyers are coming to you because they got referred your way by one of their peers. More than ever, your business case has to be sound. More than ever, you need to show CSuite proof you've solve the same problem for similar companies. Social proof makes life easier for buyer & for seller. Everyone have a great Friday!

~2 years ago, I came to Insightly because I felt like I needed more experience before taking a future next step in a management or Enterprise type role. On paper, I took a step back from an Enterprise title to "Mid-Market". But It's been a great overall decision that's going to earn me more career equity rather than a short term shot in arm title boost. Here's one of the things I've learned so much about that's going to better set up my career - The art of "negotiation". I give a lot of credit to my leader Kyle Wright for the coaching, experience. Here are the main principles: 1. Confirm that you are VOC before entertaining a negotiation round 2. Never lead with discounting or negotiate against yourself. Understand what moves the clients needle & what they are looking to optimize for. (ex. per unit cost, total cost of ownership, payment terms, etc.) 3. Make sure all asks are on the table before getting internal approvals from CFO on concession requests. 4. With meeting concession requests, always have an ask back. Examples: Contract Execution Date, Commitment to Marketing content, etc. 5. If you do all this correctly, and structure is built by client - be ready to say "no" if more concession requests come if that becomes a bad deal. Great part of all of this - this type of structure is normally really well received by the client and eliminates a lot of back and forth haggling that can prevent partnerships from happening and pushing timelines that aren't there. Still lots to learn and master - that's the beauty of career progression.

"You don't get fired for buying IBM" This is a saying that's hung around for 20+ years and has now been re-purposed for specific vendors who captured major market share in 2010s within specific software categories. The saying is suggesting that while the system has a high price tag, functionality & reliability wise, the system isn't going to cost that person their job as that combo isn't going to set off an operational bomb. "If I knew what I was getting into related to the implementation, cost, complexity of (established CRM player) - I wouldn't have made that decision. It's been a runaway freight train" - Exec at of a Fortune 500 company, based in Nashville." Question I've been asking a long time, especially in an environment where tech spend is under a lot of scrutiny- if said system causes millions of dollars of unforeseen cost & complexities, should that be a fireable offense?

It's been a 3 week hiatus for me on LinkedIn posting and in this case, that was a good thing. All my energy, focus, and brain think was dedicated to managing a few different deal cycles. To get back into things - I want to call out a trend that myself and the Insightly sales crew has really felt over last few quarters. Every deal is different. The more you're ready to go off script, the more you're honed in on delivering the best buying experience, the more creative, and the more ready you are to leverage different win zones in specific deals vs. a specific competitor - you're going to win more in this new era of selling. Example - I recently closed a larger deal (7x our normal ACV) and they had an expectation to do a first call demo & complete their buying process within a 2 week period. I can tell you, my skepticism was extremely high. any deal we've worked in the past that has these same traits - Insightly is at best a secondary option, we often times DQ ourselves to prevent allocating resources at "bad deals", and we are just being used for pricing negotiation. But since this particular client had a past Insightly user, was within our ICP, and we had solid social proof - we went into warp speed mode to demo specific config of Insightly to their team & ask some direct questions along the way on where we stood, why is this being rushed, etc. If we held to our guns and didn't do a demo on the first call, I think we would've lost momentum in the deal and let our competitors gain ground - opening the door more to lose the deal, rather positioning to win. This ultimately became a unicorn type deal where I had things working in my favor, but going at the clients desired speed and making it simple to evaluate Insightly was IMO a big reason we won. Have your "Go To" plays, revert back to strategies that won you past deals, but be ready to pivot on a dime & do things different deal over deal. The flexibility has really led to more success for our team.

Expectations are always high, selling is tougher than ever in this current environment, calendars are jammed full with Zoom meetings. Where’s the time for you? So important to have an hour or two of your days that’s all yours AND you’re finding time take a step back and be “kind” to yourself. What’s that mean? -Reflect back how much you’ve grown over past year -Reflect back on times where it’s been really hard and how you’ve always made it through -Hit Reset button on plans you’ve made for yourself, you probably didn’t get it in the timeline you wanted, and reevaluate your plan to get there and give yourself grace that it hasn’t been achieved (yet) Absolutely crucial to take care of yourself!

Usually go for the lighter, comic relief posts on a Friday...but not today. Lots of punting clients across the fence going on in the CRM space. Too many over promise, under deliver situations & a complete lack of being a trusted advisor during the sales process. Complete bullsh*t out of some of my peers across the industry 😡 Here's where the lack of transparency of vendors is causing major headaches: 🔌 Native vs. Custom Integration Clearly articulating what a native integration does vs. what it doesn't do. 90% of clients I engage with want multi-stepped integrations that falls firmly within the "custom" bucket. There are a lot of cost, resource considrations tied with these deicsions that aren't being ironed out during sales process. This triggers change orders, unforeseen costs, and threatens operational effeciencies. 🚚 Feature & Functionality Dumping Had a discussion this morning with Insightly's head of enablement Cheyenne Griffith. We both as buyers of other products are going to buy on value. If I can get more for my buck, even if it's a little more expensive, that's what I look for. When it comes to core infrastructure like an ERP, CRM, etc - if that functionality doesn't address the reason you came to market looking to switch systems OR is just a "nice to have", majority of the time that functionality sits on the shelf. Shelfware is on the top line of irritations for CFOs in 2023/2024 - functionality paid for that's not being used, hurts adoption, or impacts operations. Buying nice to haves in software leads to more negative ripple effects than positives. 💰 Transparency on TCO (Total Cost of Ownership) In supporting 200+ CRM evaluations last 1.5 years, many client come to us to consider moving off their current system. Many of them communicate to us how their annual costs have ramped up in Year 2 after sweetened Year 1 Contract. They were not privy to considerations on what would ramp them up to next plan level. And the biggest one - cost considerations related to implementation, on-going maintenance, and future integration strategy. There's the saying out there "Nobody gets fired for buying (enter established software provider)" - consequently, should a job be in question if poor decision making triggers 100K, Millions of unforeseen costs? *Steps off of Soapbox* Have a great weekend all! 😂

Toughest parts about fully leaning in to "social media" as a channel to drive pipeline as a company: ➡ You definitely won't see instant success ➡ It will be close to impossible to track how your efforts are generating brand awareness and how that drives pipeline. Here's how I know this as an AE working for a company that's moving upstream, in a highly competitive space, against of of the most recognizable names in SaaS: 1️⃣ On a phone call where I'm calling to displace a current system - head of RevOps mentioned "I've actually heard of you guys and you put out great content" (200K of Future Pipeline) Displacement selling is the majority of the game more so now than ever. Loved a post yesterday by Santosh Sharan on this topic as this is truly felt. 2️⃣ Recent inbound lead that came into Insightly - "Ive seen Insightly because of Samantha McKenna (friend of the pod)" (~40K of Pipeline) These are just two examples. Some of this can be tracked and the other 90% of the goodwill that is generated from your content you probably can't fully connect the dots. Outbound is just a different motion these days.