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GTM Navigator is our ongoing series where we break down the essential components of nailing the right go-to-market strategy.  

In this episode, Allison Williams, Operating Value Associate at Fin Capital, speaks with Javier Ramirez, GTM Advisor and Fractional CRO at Cuota, a GTM advisory firm that has helped over 55 B2B SaaS companies increase revenue by optimizing sales. Javier’s extensive B2B sales leadership experience, honed at Zenefits, Rippling, and WeWork, provides unique insights into developing successful outbound sales strategies. In this discussion, you’ll gain a better understanding of the pivotal strategies for structuring and executing outbound sales that adapt to various business sizes and stages. We’re grateful to Javier for sharing his insights and hope that this episode of GTM Navigator empowers you to enhance your outbound sales effectiveness. 

Key Questions Discussed:  

Transcript (edited for clarity):  

Allison Williams: Thank you so much for taking the time to speak with us today. We’re excited to have you on to discuss all things outbound sales. As a firm, we work with companies across the venture lifecycle. As you can imagine, the go-to-market motion can really change over the course of a company’s lifecycle. So we thought it’d be great to have you on as your experience is very relevant to growing and expanding your GTM motion. So with that, would you mind sharing a bit more about your background, what led you to start Cuota and what Cuota can help companies with? 

Javier Ramirez: Thanks for having me, Allison. I started in finance as an analyst at Goldman Sachs, then moved into sales and trading. Driven by a desire to build and perform, I transitioned to Silicon Valley in 2013, joining early-stage companies like Zenefits and Rippling, where I led enterprise sales teams focused on outbound strategies. After various roles, including a VP of Sales position and leading enterprise sales for WeWork in the southeast U.S., I founded Cuota in 2020. Cuota helps Series A and B fintech, enterprise software, and B2B SaaS companies in the U.S. and Latin America optimize their sales strategies, particularly in building effective sales teams and structuring sales organizations. So I’ve been doing that for four years now. We’ve worked with over 55 venture backed companies, have a lot to share. So fire away, if you’re curious about anything in particular. 

Allison Williams (02:53): That’s a fantastic background. Given your experience with 55 companies in four years, could you start by defining outbound sales and how it differs from other sales types? 

Javier Ramirez (03:21): Outbound sales involve proactively reaching out to potential customers to demonstrate how your solution addresses their business needs. It includes various tactics like cold calling, cold emailing, social selling, networking, and even direct mail. This approach differs from inbound strategies like marketing-generated ads as it involves a direct push to engage potential clients who may not yet recognize the need for your product. 

Allison Williams (04:12): When should a company initiate outbound sales, and who should be responsible for these efforts at different company lifecycle stages? 

Javier Ramirez: Outbound should start as early as possible due to its time-intensive nature and the need for iteration to yield results. Initially, founders should lead sales efforts to gain direct market feedback and refine messaging. As the company grows, transitioning to a team-based approach is crucial, starting with hiring SDRs to support outbound efforts, allowing founders to focus more on closing sales and managing trials. Over time, this responsibility shifts from founder-led to sales-led as you hire sales leaders to oversee the growing sales team. 

Allison Williams (07:02): Great. Super helpful. And how do you think about the differences between outbound sales for B2B enterprise motions versus B2C or B2B SMB? I know you’ve had a lot of experience in B2B enterprise, but they’re obviously very different motions. 

Javier Ramirez: B2B enterprise strategies are highly targeted and often involve account-based selling where the stakes are high due to potential contract values. Strategies like ‘go low, go high,’ where SDRs and account executives collaborate closely, are common. B2C strategies rely heavily on marketing to drive traffic, while B2B SMB focuses on volume through multiple channels to maximize reach and conversion. 

I’ll start with B2B enterprises. Obviously as you mentioned, it’s the one where I spent a lot of my time in. The first thing is that the stakes are high. You’re going after big companies with big contract value potential. And what it tends to happen is that you go for what’s called an account based selling approach. And so you have usually an SDR that might take a look at 10, 20 companies that they really want to get into, and they get very tactical but very strategic about what their approach might be. In this situation, you might also have a pod. And what a pod is built around is you have an SDR that’s pegged to an account executive, an enterprise account executive. 

And those two work as a couple. So you send the SDR to go to a person that maybe is not the VP, maybe it’s not the decision maker, and he can gather as much information as possible. So the SDR gets as much information as possible comes back to the enterprise account executive. Now, the enterprise account executive has a lot of feedback on what pains, priorities, needs are for that specific company. Now that enterprise account executive can maybe go to the VP with a more specific approach. It becomes the most tailored, most successful or highest converting way to get in front of those companies. That approach is not about volume, it’s about conversion. And because of the high ACV nature of these deals, if you close one of them, that could be game changing for the company.  

In terms of B2B on the SMB side, it’s more of a volume-based approach. The difference here between that and enterprise SMB, because you have less decision makers, usually a low ACV type of environment, most SDRs or teams that are doing outbound sales will look to use tools like Ample market, tools like Apollo to build email sequences, but that are spread across different channels. So you’re just trying to solve for where can I get in front of this person with the most success. I’m going to try to spread my efforts to get the highest conversion through one of those channels. That becomes a very numbers-driven approach. Of course, the construction of the messaging and the strategy are extremely important, but very different than what I described for B2B enterprise. 

Allison Williams (10:57): That leads nicely into our next question. I’m curious how you think about — on outbound — balancing personalization with efficiency while still differentiating yourself for others? If you’re targeting only a few large enterprise customers, you can be a bit more hands-on, but maybe you’re targeting enterprise customers and smaller businesses. How do you balance it? 

Javier Ramirez: There are two things that are best practices and that people miss on. One is strategy, the second one is messaging. From a strategy standpoint, even if you think that it’s low risk where a lot of people are just sending out messages for the sake of it, you’ve got to understand what’s going on in the market. It’s noisy out there, a lot of people that are using the same tools, obviously there’s AI copywriting tools now that build messages on your behalf. It’s good for you to know where your competitive approach is and how you can differentiate. 

Where do my buyers spend the most time? That is a question a lot of people don’t spend enough time thinking about. I’ll give you a very persona-specific example. Engineers don’t like to be on the phone. You usually don’t call an engineer. I look at some companies that are developing their outbound strategies and in includes selling a product to engineers and doing a hundred calls a day. That’s not going to work. Engineers are not picking up the phone. You must do an email-first approach to make sure that you’re getting as close as possible to them. And then of course, what do they care about? Which leads me to the next point, which is the messaging. 

There’s a very simple messaging framework called AIDA (attention, interest, desire, action) which many successful companies use. A lot of people are on the phone nowadays, but they’re also looking at organizing their inbox based off what they see as a subject line. And that’s the deciding factor for them to decide, am I going to open this email or not? Really spend time on that hook, on that initial attention grabber, because that leads you in a waterfall format to continue revealing more information.  

And don’t waste real estate. Things like, “Hope you’re well”, “How are you doing?” If I don’t know you Allison, and I’m trying to get a meeting with you and I’m telling you, “Hope you’re well,” I know you’re coming to sell me, so I’m going to delete your email pretty quickly. That opening line then driving you to the second sentence, and then of course the call to action, are all critical. People don’t spend enough time constructing a message that’s worthwhile. 

Allison Williams (14:19): Curious on the opener and closer, are there ones that you’ve seen kind of work well across a lot of organizations so you don’t have to necessarily personalize to the person? Or are some of the tools that are out there now able to help you personalize them even further? 

Javier Ramirez: I’ve seen many things work. Again, it depends really on the buyer, persona industry, and also geography. What works in London and US, versus Mexico, might be different, but across the board, I think that the more personal and less salesy they sound, the better. So it might be “Fin Capital <> Cuota,” it might be “Meeting request,” it might be “Sync”. The ones I would definitely avoid would be the ones like “Cuota, let me help you increase your sales” or “The most effective AI tool in the market” or “Are you not converting outbound emails?” The types that tell you that somebody’s coming to sell, you don’t tend to convert pretty well because people don’t like to be sold to at the end of the day. 

Allison Williams (15:42): Are there any other key mistakes? You’ve mentioned some, but are there any kind of other key mistakes in general that you would look to avoid on outgoing sales? 

Javier Ramirez (15:53): A key mistake is failing to match the sophistication level of your prospects, especially in industries like fintech where trust is paramount. Outbound sales should convey professionalism to build credibility and trust from the first interaction. 

When we talk about financial movement of money, it requires a lot of trust and the startups or even the growth stage companies need to earn that trust from the minute that they send the message. You have to meet, match, or exceed that level of sophistication when you show up. That would be one of the bigger ones that a lot of people don’t talk about. 

Allison Williams (17:34): That’s very helpful, and a lot of the companies we talk to are selling into banks or other large financial institutions where maybe the culture of a startup versus a bank is of course very different and important to understand those nuances. 

What do you view as some of the most important metrics to monitor and can you share any realistic targets to hit for these? I know it’ll change of course across companies and across life cycles, but curious what you focus on the most. 

Javier Ramirez: At the end of the day, the northstar for an outbound sales team is qualified meetings booked. Any SDR that’s fully ramped should be booking 10 to 15 net-new qualified meetings booked on a monthly basis. What happens, is that a lot of people will look at open rates. Open rates really don’t tell you that much because if you send a bunch of emails, a 60% open rate doesn’t really tell me a story. I’m really looking at my reply rate or what did I do with those metrics? 

From a sales management standpoint, you need to help your SDRs correct those behaviors. There are so many tools nowadays that help you understand open rates. If you see someone has opened your email three times, give them a call, build the relationship. Of course, I think that the question you haven’t asked me related to those metrics is, “How do you scale that?” There are diminishing returns when it comes to outbound. Adding 10 more SDRs or 10 more account executives that do self-prospecting doesn’t necessarily translate to 10x meetings booked.  

Allison Williams (20:31): Finally, thinking about your first sales role, what is one thing that now that you wish you knew at the time? 

Javier Ramirez: I’ll tie it to outbound. One of my first outbound campaigns, I did with the help of the CMO at the company. I got a couple of responses, but was frustrated. He asked me why and reminded me that no one is going to respond to your email with a definitive, “Hey, yes, I want to buy.” 

Even if someone responds “no thanks,” that’s a response. That’s an opportunity to say, “Listen, we’re gathering feedback. We’re new to the market. I’d really love to understand what made you not want to take a meeting with me.”  

I say this because from an outbound standpoint, a lot of sales leaders, founders, even SDRs, will send an outbound campaign and expect that somebody’s going to respond and say “Yes, I need a new sales leader. Let me get on a call so you can tell me how you can make my team better.” It’s not like that. Obviously, it’s one of the things that I had a false expectation about coming from finance with a big brand behind me. And when you work with startups, you don’t have that brand behind you. The challenge is a lot greater. 

Allison Williams (22:34): Thank you so much for taking the time to join us. That’s all the questions that we had today. I’ve really enjoyed this conversation and I look forward to discussions in the future! 

Javier Ramirez: Awesome. Thank you. Hope everyone enjoys it.