Software sales is changing….rapidly. Seasoned veterans who rely on relationship building and vendor preference aren’t cutting it in the SaaS world. Companies are now able to choose products that solve one specific business problem, without requiring a whole suite of products or being locked into a specific vendor. From a sales prospective, that means going back to sales basics: knowing your buyer, prospecting, building value, and not relying on as much on connections to make the sale. You have to perfect the craft in a modern way.


If you have heavy Sales Development training, but you have less closing experience, you should go for an early stage startup in a new industry. This requires more prospecting than closing experience, as it will require evangelizing the product more than anything...a development heavy position is best for you.

Have you sat out on picking up modern selling techniques like social selling? Is LinkedIn and SFDC new to you? Maybe a more established company with full marketing support and a dedicated SDR is right for you.


Have you sold this product before…who cares? If it’s an innovative or disruptive product, nobody has sold it before. At the end of the day, sales is sales; however, ERP or InfoSec salespeople tend to struggle in the HR space and vice versa. It’s not as focused on the product, as it is about connecting with the buyer and their needs. For example, HR is a very different space than selling to IT, so it requires an Account Executive that can do more hand holding as a Trusted Advisor in the HR space, since they are new to buying software for non-core systems.


Pay attention to whom you’ll be working for beyond just the company. It’s also not just about the product, as it’s just as important to look at the leadership. Is there a specific sales methodology that they are following, such as Challenger Sale? Does the leadership want a smile and dial/bang the gong salesperson, or are they seeking someone with advanced territory management doing in-depth research? Pay attention to the day-to-day and how much you can adapt to it more than the technology itself, which will always be changing.


This is easy…..aim for market rate base and uncapped or performance driven commission. Base is meant to pay your bills, and you shouldn’t be concerned about that if it’s market rate. Sales is all about the upside, so what are the deal sizes, sales cycle, percentage of closed pipeline per territory, ramp quota in the first year, regular quota, and percentage of team hitting or exceeding their quota? Make sure you’re set up for success, and that will be able to crush whatever quota has been set.

There will always be a need for sales; however, the duties and focus of their need has changed with self-serve and à la carte SaaS options. Non-Enterprise software sales is becoming increasingly automated, but there will always be a need for an Enterprise lead on a 1MM+ deal. Business/Sales Development will always be needed on some level, and there are blurred lines between Sales and Marketing with social selling and ABM as the new standard. Sales people are needed for the first and last 20%s of the sale, as someone needs to introduce the product and work on contract negotiations at the end. The middle 60% is becoming automated, and the development role will automated soon too. If you’re looking to break into sales or on your way out, play to your adaptive strengths above all else. It’s not about being young and hungry or experienced and connected anymore, it’s about who can play smarter. Your recruiter can help navigate these finer points to help you find the right fit, so be sure to discuss all of this before walking into your next sales interview.