SaaS selling tips — Sales Engagement

It should come as no surprise to hear that sales is being disrupted by tech. For startups looking to quickly scale their sales operations there are hundreds of SalesTech tools to choose from. This list has some of my favorites.

One growing category of tooling is Sales Engagement. These platforms help sales teams manage and scale quality lead funnels with outreach automation.

Sales Engagement

One of the most popular tools in this category is Outreach.io (now a unicorn). The leadership team at Outreach recently published a book on the subject. It’s not heavily focused on their tool (which we use at Sqreen), but rather shares seasoned advice about building a top-of-funnel sales machine. It’s a solid reference for B2B startups on how to build a modern sales strategy with specific tactics on how to engage with leads. Because we’re book people at Sqreen, I had a chance to read it and wanted to share some takeaways.

Scroll down for the tl;dr summary.

Revenue efficiency

Like all machines, the sales funnel needs to be data-driven. A key objective for sales engagement data is to show revenue attribution. All the revenue metrics should be able to be traced back to the top of funnel source (resource download, product signup, outbound prospecting, etc.) Revenue metrics include things like opportunity $ created (“pipeline”), ARR closed won (and lost), the ACV (average contract value), and the average sales cycle (time to close from opportunity creation).

The goal is to be able to answer the question: “What resources do I need to deliver $X of new pipeline next quarter?” The answer will be different for each lead source (e.g. inbound vs. outbound).

Account-based Selling

Account-based selling is about building relationships, regardless of whether or not there’s an active buying process. The idea is to drive engagement in large accounts with multiple buyers through marketing, sales development, account executives, and customer success functions.

The first step in a successful strategy is defining your Ideal Customer Profile (ICP). This is required for account sourcing (targeting) and focusing sales activities on the accounts you can close. This could include a description of your target accounts’ size, industry, geography, technology in use, Alexa rank, business challenges, etc. Get granular with the ICP. You may end up with a few, that’s ok, just bucket your ICPs according to your value propositions for each.

Next is gathering data & intelligence about the account and the hierarchy of contacts in your ICP. Use a database like DiscoverOrg to pull accounts and contacts to go after. Some people call it “hunting”, I prefer to call it “helping”. These ICPs need you and your product!

As you develop a sales strategy, it goes into a sales playbook. It’s the SOP that will help new sales reps get up to speed (sales hires usually get a “ramp” period to grow into their quota). The sales playbook is a collection of ideas for developing the buyer relationship according to your specific product/sale, with information on how to communicate the business values, the buyer’s journey, how to leverage product usage in the sale, how to deliver the deal proposal, your sales rules of engagement, etc.

Balance email quality with quantity

The holy grail of an effective outbound sales strategy — personalization at scale. There are a few categories to shape a personalized message around:

• the account — e.g. recent news headlines, or business/industry specific challenges. It can be used for personas across the organization. Beware, messaging can be off target (organizational goals don’t always align with individual goals).
• the persona — e.g. goals/challenges of their role or legacy technology in use. This messaging can be applied across different accounts. Beware, the same title at a different company can have different responsibilities.
• the individual (hyper-personalization)- highly effective. Use LinkedIn, news mentions, blog posts, podcast guest visits, etc. Beware, time-consuming, don’t be creepy.

Email copy

It might be worth investing in a professional to do this. It’s an overlooked component of effective outreach. To get the highest level of engagement, your copy needs to be relevant and spot on. So if it’s so crucial, why might you want to outsource this instead of asking your sales reps to do it?

• Reps don’t have time. They should be spending time actively prospecting and engaging with prospects.
• Miniscule increases in reply rates and conversions at scale translate to huge pipeline increases. Take 250 emails sent per week — an extra 1% reply rate over 6-months is 62 additional conversations.
• Writing is not a sales rep’s forte (fun story — my friend in content marketing had to remind me to put an apostrophe here).

If you decide to write your own outreach emails, have a value-driven sequence storyline like an Oscar-winning film. Focus on buyer needs, not your solution. Use multiple emails that build on each other, slowly unveiling why your prospect should be working with you right now. End with a climax (call to action). Develop a connection before asking for their time. Why should they trust you? Bring value first and try and help them relate to your brand.

But don’t spend all your time on emails and phone calls. This is the era of social selling. LinkedIn (Sales Navigator) and Twitter need to be part of your sales strategy (not just marketing strategy).

Automate (almost) everything

The goal is to remove administrative friction keeping salespeople from actively engaging with prospects. For example, you don’t want salespeople (SDRs, AEs, etc.) enriching marketing leads with more information like title, phone number, business email, etc. Use an enrichment tool like Clearbit or LeadIQ, or hire an intern.

A sales engagement platform lets you automate outreach on a schedule, with the option to include manual steps like following up with a personalized email or LinkedIn message. The outreach we do at Sqreen is a mixture of hyper-personalized messaging and automated follow up emails. Because we’ve defined buyer personas, even our automated emails have a personalized touch.

In Summary

The Sales Engagement book was packed with best practices, I only mention a few things here. There’s a lot of anecdotal advice that resonates with trends for selling to larger businesses (enterprises), but the methods mentioned would take a different shape if selling to smaller business and startups. How people and businesses communicate and buy products is constantly changing and makes a successful technology sales machine a moving target. Iteration is key for sales as much as it is for product.

Tl;dr

1. Optimize for how buyer’s buy — omnichannel and hands-on. Align marketing, sales, CS to the same buyer’s journey.
2. Revenue Efficiency — know customer attribution. Align metrics across the org.
3. Get to a point where reps only do selling activities. Automate (and leverage UpWork)!
4. Build consistent, repeatable data-driven processes.
5. A modern tech stack helps increase sales rep ramp time.
6. Have a framework in your sales playbook for A/B testing everything in the outreach process.

About me

I’m a tech nerd doing small business sales at Sqreen, an application security SaaS startup based in San Francisco and Paris. Ping me to chat SaaS sales strategy. Thanks to Alison Eastaway and Josh Dreyfuss for the writing tips.

tyler@sqreen