Founder GTM Stories

Paid’s Journey to Building an Enterprise Sales Motion

Posted: 1 July 2022

In this interview, we spoke with Natasha Foster, the co-founder and COO of Paid about the evolution of their go-to-market (GTM) strategy. This Q&A applies to any founders building products for the enterprise and looking to transition away from founder-led sales. 

Sneak peek – 5 takeaways:

  1. You can’t build a best in class sales journey without a Customer Success team to drive a best in class customer experience. Customers buy from people and want to know they’ll be taken care of
  2. To close enterprise deals, encourage the customer to share their ideas for the future of the product & make them feel part of your product growth journey. Treat them as design partners!
  3. Agree KPIs with the customer before kick starting the pilot! Set timelines, front-load as much of the commercial negotiation and get all decision makers on the mid trial review
  4. Qualification and selling is all about shaping the process around your prospects’ needs, not yours (as tempting as it may be to drive your own agenda)
  5. Ask the hard questions on qualification calls and during the pilot to get to the nitty gritty of the customer’s pain. “What’s your nightmare scenario? What would prevent you from adopting the solution?”


Who are you and what’s Paid’s mission?

I’m Natasha, co-founder and COO of Paid. My co-founder and CEO is Tom Howsman and we founded the Company in 2019. We help enterprises procure from small suppliers. Today, the procurement process for large enterprises is lengthy and manual. That’s why it’s frustrating and a real blocker for business. For example, onboarding a new supplier usually takes months! With Paid, it’s done in minutes.  

Paid injects magic into procurement and turns it into a process that people love. How? It creates certainty and security on the supplier side. On the buyer side, it allows you to gain control of your business and turn procurement into a profit centre. Your team can finally focus on what matters and add value, by negotiating mega discounts rather than dealing with non-strategic suppliers. What we really want is to take procurement out of procurement – to enable permissionless procurement for low risk contracts.


Where are you in your GTM journey (company size, traction, who’s selling, how you got there so far?)

Tom and I started as a duo, in the trenches together leading sales to large enterprises from the get-go (2020). We realised that only one of us needed to be accountable. I had no background in sales. But I can speak to our procurement buyers as a peer, having worked in large corporates and seen the supplier onboarding process first hand. I also know what it feels like to be a small supplier, having worked at a small company partnering with large corporations. Naturally, I turned out to be the one driving sales. Founders need to own sales initially to deeply understand the product and pain point.

Our first commercial hire was a Business Development Manager (‘BDM’). We had no playbook so early in our journey. That’s why first commercial hire was working with me 50% on SDR-style work and 50% on strategic GTM support (driving analytics/research, AB testing our messaging, testing sales tactics). We also brought in an ex consultant early 2021 to help us push the process along. Those initial sales efforts led us to landing 3 very large enterprise clients, including BT and ISS. 

Onboarding those clients made us realise that we couldn’t build a best in class sales journey without a Customer Success team. We recruited a CS expert to be laser focused on the customer experience and community. 

Throughout each sales process and onboarding, we learned which stakeholders we should be targeting, how to adapt our communication with them and how we help them achieve their goals. Today, we feel we deeply understand our prospects’ challenges and pain points. At this point, we feel it’s the right time for Tom and I to transition away from founder-led sales. We plan to hand over sales leadership reins to a Head of Sales who will hire SDRs and other sales reps. We’ve actually tried to hire a sales leader early on, but it was just too early for them from a pure sales perspective. They’re usually driven by metrics and comp!


What’s striking is that your very first customer is one of the largest organisations in telco. Many mature companies simply cannot close such a deal due to its complexity. Can you please share with us how you closed this first customer?

It took a lot of cooperation, organisation and perseverance on both sides! We had strong champions within the organisation – both at a senior level (we got the most incredible support from the Chief Procurement Officer) and at the operational level (Procurement Manager implementing the software). 

Although Paid has an easy integration and implies no change in users’ behaviours, decision making on the enterprise side is still highly complex. Plus, you need to find the right balance between pushing proactively to create urgency and exercising patience. Things take time in enterprise sales! You don’t need a sales background to understand that. 

We spent a lot of time with our first and second enterprise customers to (1) truly understand the pain points they were experiencing (that we could solve!) and to (2) find where the cost associated with the pain points was located. We then tailored our proposal to customers based on what they’d find most attractive, and to match the pricing (and who paid for the product) with the location of the cost drain! 

Finally, to close the deals, we were very flexible about the ‘art of the possible’. Whilst we were careful to avoid promising bespoke development, we encouraged the client to make ‘suggestions’ for our product roadmap, to get them excited about being part of the product’s developmental journey and to make them feel special in getting a software ‘just for them’ (even if from our side it actually wasn’t bespoke!)

Also, once the deal is closed, you can’t leave the account to just become successful on its own. It was crucial for us to keep building deep relationships with customers post deal completion. This is why Customer Success is so important in enterprise sales.


Do you remember the very first step you took as a founder to start taking your product to market?

We were lucky to be introduced to senior procurement professionals by our investors. We sold the dream of what we could become, leveraging creative language to bring to life how our software would fundamentally change the life of procurement teams. This is despite the fact we didn’t have a product at the time!

One of our very first initiatives was to build brand awareness by publishing Q&A blog posts. We looked for the most open-minded and innovative people on LinkedIn, deeply focused on transformation and change. We invited them to Q&A sessions. We got a 50% response rate on our cold emails! This validated our thinking around the fact that procurement truly is an under-appreciated function.

Some of those conversations turned into sales opportunities and awesome sources of information to help us sell better. Ultimately, the Q&A evolved into our podcast “Procurement Trailblazers”. We love shining a spotlight to show the value Procurement teams deliver.


We can’t really talk about enterprise sales without mentioning pilots. Pilots are an important part of the sales process for Paid. Can you walk us through the pilot process and the key learnings you’ve accumulated to increase conversion rate?

In the beginning, we had the age-old dilemma about whether we should run free or paid pilots. 

Our first pilot was free and we literally ‘let it happen’ – no prescribed process and success criteria. We only instigated commercial discussions towards the end of the pilot. We managed to close the deal but it took a lot longer than we wanted. We realised 2 things: 1/ it’s key to define KPIs upfront by flagging what clients are most excited about; 2/ if you structure the pilot well enough, having a free or paid pilot doesn’t matter too much.

In our second free pilot, we proactively defined KPIs with the client before the pilot even started. The client signed an opt-in contract whereby they had to express consent at the end of the pilot to continue as a customer. This time we front-loaded the commercial discussions, but it still took an additional month to get everything finalised. 

Lesson learned – we need to be laser focused on conversion half way through the trial (and not wait until the end)!


How do you think about the role of Customer Success in pilots?

The Customer Success team should work with the customer on the pilot from day 1. Paid is about adoption – training users to leverage the software even before the trial starts saves time. And the most important thing: you should hone in on what the users personally care about achieving, rather than the value you envision adding. 

All in all, a successful pilot implies a close collaboration between CS and Sales – the Sales rep should identify the decision makers and how to secure time with them. Plus, don’t underestimate the importance of having all decision makers attend review sessions throughout the pilot, to secure their ultimate approval!

Today, we moved on to paid pilots whereby we price the trial the same as the subsequent contract to create a smooth transition. We also run mid trial reviews with all decision makers in the room to share the value of our product. It’s a great way to get user feedback and solid quotes from users and suppliers.


Putting things in perspective, what would you have done differently and why?

We should have better structured the pilots from day 1, setting up clear objectives and timelines. We realised that the best way to sell is to deeply understand your prospects’ needs and drivers, and constantly show how your software helps them get closer to their goals (and not yours!). We learned it’s very important to understand the structure of the organisation and who’s going to see the value from Paid. Do your best to involve these people in the decision-making process (and the ones paying for the product!)

Finally – don’t be afraid to ask the hard questions to get to the bottom of their pain points and needs – “What’s your nightmare scenario? What would prevent you from adopting the solution?” This is the only way you get into the nitty gritty of things and position your product efficiently.


What’s been your biggest challenge and how did you deal with it?

Our biggest challenge has been twofold:

  1. Reaching the “aha moment” with enterprise prospects: we needed to introduce demos earlier in the sales process to help them understand the value of our solution.
  2. Navigating the lengthy enterprise decision making and implementation process. This is still work in progress! To date we’ve tackled this through aligning our pilot and contract pricing, investing in rapid deployments and setting out a timeline for implementation & success criteria for trials. On this, Crane helped us think about pricing as a lever to accelerate the sales process. Their experience across pricing and GTM strategies got us to AB test approaches to achieve the right structure (for now). They challenged our GTM strategy where needed. Especially around the best way to transition from a trial to a full contract.


What are the top GTM books that you’d recommend to other founders?

  • The main one is “Influence (the psychology of influence)” by Robert Cialdini, because I love the psychology of persuasion. Great read to understand how people are influenced to do things, all based on statistical surveys.
  • “Never Split the Difference” by Chris Voss. Great advice on structuring pricing and having commercial conversations.
  • “Drive” by Daniel Pink. Ephemeral – very interesting author. 

All 3 books speak about needing to understand what the person on the other side actually wants (vs. what you think they want).