Whether it’s hiring top talent, strategically positioning products, building effective demand generation funnels, or understanding customer needs, Jess Forrester is a seasoned Chief Marketing Officer with a proven track record of success in the tech industry.

With a wealth of experience in demand generation and product marketing across various sectors, including SaaS and EdTech, Jess Forrester has held prestigious CMO roles at several prominent firms, successfully leading through high-growth phases. Most notably, she led the marketing efforts as the CMO of Quorum, a highly regarded public affairs software company with an incredible scale story. 

Crew Capital recently hosted a roundtable discussion featuring Jess Forrester, where she shared invaluable insights with our portfolio companies. The discussion covered best practices for founders, including strategies for building marketing operations and demand generation, hiring the right team, product positioning and how to build the ideal customer profile. 

Think long and hard about the Ideal Customer Profile (ICP)

In the realm of product positioning, one common mistake businesses make is adopting a broad approach to the ICP — sometimes this comes from founders selling a large Total Addressable Market (TAM) in fundraising conversations. Forrester stresses the significance of defining a tight ICP that aligns with a startup’s current goals and capabilities. By narrowing down the positioning, companies can avoid missing out on valuable opportunities with potential customers who are facing the specific challenges the product solves in the present. If it is hard to identify which of the current customers are best-fit, sales calls are a helpful resource. If closing a deal feels oddly easy, there’s a high chance that the customer’s needs are aligned to the company’s value proposition. For marketing teams, having the sales team extract highly valuable pieces of information gets them closer to understanding their ICP. Instead of lofty ideas, companies should seek details from customers to effectively target their ICP and position their product in the market. Additionally, understanding the attributes specific to good-fit customers is crucial when segmenting customer profiles.

Create the right context and positioning to generate demand 

When positioning your product, leverage context the buyer already has to reduce friction.

Think of April Dunford’s example: selling “dessert on a stick” paints a very different picture compared to saying, “it’s like a lollipop, but it’s made of cake”. In this instance, the former confuses the audience (why would I put a slice of cake on a stick?) whereas the latter creates an instant visual image of what the product actually is. The buyer is able to fill in a familiar context, thus closing a huge gap between perception and reality.

Additionally, talk to customers to understand the category they’re putting you in. Users can often put a product into a category that clashes with the company’s own view of its product. If the company thinks they’re in one category, but its customers associate it with another, they may be onto something that might help the company get the positioning and context right.

Getting the hook right for demand generation

The entire marketing organization should share a goal of finding powerful hooks. Focus relentlessly on testing and learning. One of the biggest mistakes that early stage teams make is to not spend nearly enough time understanding what hooks are working — they test channels like crazy, but the offer is could be wrong. It’s also crucial to figure out what the company should and can be known for, and what the audience really cares about in order to become a brand that they want to associate with. 

Set goals that make sense for your maturity

While some people think of the audience as a “vanity metric,” building an accessible audience is a great place for the marketing team to start. Marketers have overcorrected to concerns about their top-of-funnel goals being “vanity metrics,” and some set goals too far down the funnel. A revenue goal can work in the early stages of your marketing organization if you have a very short sales cycle — but in most cases, you need to start higher in the funnel while you improve predictability and process adherence in between. For example, “first meetings with a new account” tends to be a good first demand generation goal — but make sure the first meeting with a new account can be counted as a separate occurrence from the second or third one in order to measure them correctly. At an SMB organization, you should specifically track how many of those meetings come from inbounds / “hand-raisers” who indicate interest in your company by offering their contact information.

Hire marketers that can scale with you

In high-growth SaaS, in particular, you need to hire people who will be able to stick with you through rapid change. Look for T-Shape type profiles, which means they have some breadth of experience — usually from a generalized role where they owned all aspects of marketing — and they have at least one and preferably two aspects where they have deep knowledge in. The depth of experience should align with the company’s current marketing strategy, and the breadth will allow them to pivot.

Hiring for a marketing role — or for any role — is an arduous task and requires a multifaceted approach. First, understanding the product and ICP is a prerequisite for hiring the right person for the right role. Once ready to hire, a good approach is to think in terms of looking out for flags. Decide what constitutes a red flag and what should be seen as a green flag. One red flag to consider would be a candidate who focuses too much on barriers to success. For example, someone who blames others by focusing on external matters. It’s also important to be mindful that you aren’t persuaded by confident candidates; it’s important to probe to find out what the candidate knows and has done and how deep this knowledge is rather than taking confident answers at face value. Trust, but verify.

Some green flags to consider would be taking pride in execution, exhibiting a sense of ownership of their work and decisions, showing recent examples of seeking knowledge, such as finding novel ways to use new technology such as AI, and in general showing a keen interest in adopting new things. Another green flag is a candidate who can speak to the function more holistically. An SEO person should know SEO but also have a good understanding of other aspects that go into marketing, such as product and growth efforts. In most cases in SaaS, your first marketer should have at least a little bit of SaaS experience. Hire a doer who can do the 10% you know is needed and who can figure out the other 90%. For mid-market/enterprise, a strategic product marketer who is a strong writer and has an interest in learning the full function is a great choice. For SMBs, an inbound marketer or demand generation expert may be a better choice.

Ask the right questions

Asking about a professional failure is a wonderful question because it reveals who the candidate is, how the candidate thinks about failures and their ability to process information — positive and negative.

Here are some additional questions to consider and to reduce chances of hiring an unfit person for the job:

• Tell me about your biggest professional failure
• Tell me about the last time you solved a problem
• Tell me about a time when you had a wild idea and made it happen
• Tell me about a process you built and how you built it

When it comes to the all-important reference call and speaking with the candidate’s previous managers, it’s crucial to ask at least one question: what should I know to be good at managing this person? In addition to revealing gaps, this question is a great way to help managers find quick resolutions to potential conflict situations and find ways to develop mutual trust.