Relate started as a product for startups and small businesses. Realizing that moving up in the market accelerates product development and generates revenue quickly, we decided to also build for enterprise customers too.
Today we have several enterprise customers paying five-figure subscription fees. It all started with closing one customer we reached out to as part of our outbound campaign.
Here’s a case study on the Relate team’s first enterprise deal. It details the process from prospecting to closing the deal and onboarding.
Prospecting
1/ Multi-threading: A year-long journey to book the first meeting
Our engagement with this customer exemplifies the persistence and strategic approach required in enterprise sales.
It started when we saw a job posting for a B2B sales representative at the company.
This was a key indicator. Hiring for such a role typically signals current sales success or strategic growth.
We saw an opportunity to introduce our CRM product, so we reached out to the contact to initiate the process.
Our first cold email didn't get a reply, as with any good story.
A few months later, we connected with another executive through our marketing channels (e.g., blog posts, newsletters, etc.).
We reached out to both of them again, at the same time, in separate threads. One for the existing contact, the other for the executive we found.
This is what salespeople call “multi-threading,” a strategy to find the right decision-maker quickly.
When this attempt also went unanswered, we followed up three months later.
We made sure this was shown as persistence, not intrusive or annoying (check out our best practices on cold mailing).
The breakthrough came a year later when the company’s marketing lead signed up for a demo (inbound).
We couldn’t book a meeting immediately, but we followed up for two months, seeking an introduction to the right decision maker and asking for a demo.
Turns out, they were looking for a CRM. We succeeded by sending them messages about how we can help with CRM implementations and migration.
This allowed us to position our solution in their impending CRM implementation, ensuring consideration alongside other tools.
2/ Initial discovery call & product demo
Before our first meeting, we thoroughly researched them, digging up information such as:
Company and service info
Investment history and present status
Customer volume and types from relevant articles
Info on meeting participants from the company blog and LinkedIn
During the meeting, we gained valuable insights:
The company’s organizational structure, especially how sales and marketing collaborate.
Business problems solved through CRM implementation
Prioritizing requirements
Their decision-making process and timeline
We identified three critical pain points this company needed to solve:
Centralizing customer data on a single platform
Managing the entire sales process from lead generation to sales and customer success.
Supporting user adoption of a new tool and process through simple UI/UX and robust support with personalized onboarding and training for a smooth CRM implementation.
Our product demo was concise and targeted, addressing three key priorities.
The approach resonated well with them. They said our solution seemed to be the ideal fit.
Closing the deal
Our champion said our CRM was better than Salesforce, HubSpot, and Pipedrive, so we expected a quick closing. We expected them to move forward within a month.
But the deal didn’t close right away. After a few days of going dark (obviously we followed up religiously), the customer came back and told us they wanted to introduce a new alternative and compare it with Relate.
They presented additional requirements that extended the sales cycle and required more work to win the deal.
1/ Helping champions convince stakeholders
Over a month, we exchanged over 40 emails, mostly with the champion.
They shared with us how internal discussions are going, and we discussed how they can address internal objections. The champion circulated our references and persuaded their team.
During this process, we prepared well-written business case documents, action plans, product demo recordings, and any resource our champion needed.
Having a champion as our proxy was invaluable in navigating the decision-making process, since we couldn’t sit in on every single discussion meeting held internally.
2/ More discovery calls and product demos to understand requirements and priorities
To win this deal, we had to persuade not only the sales department but also marketing and customer support teams. Inenterprise sales, it’s often multiple departments involved in the decision-making process.
We asked our champion to arrange meetings with cross-functional departments for deeper insights into their needs and challenges. During the meeting, we addressed their concerns and tried to tailor our demos to their needs.
After the meetings, we helped the customer prioritize sales, marketing, and customer support requirements and align on areas needing further feature development. We actively participated instead of waiting for their decisions.
Enterprise customers often want custom features and integrations. It’s crucial to show that you can deliver some of these requests and how quickly.
This helped us stand out from other alternatives.
3/ Use a mutual action plan to manage communication.
Since the first discovery call, we had more meetings, emails, and hundreds of Slack conversations. Needless to say, the deal was not done!
This called for a centralized, accessible source of truth for all resources and the project timeline.
To address this, we created a shared workspace for a Mutual Action Plan (using Coda). This document summarized our discussions and decisions, outlined specifications and development timelines for features needing further work, and detailed our onboarding requirements and schedule. This approach ensured clear communication throughout the sales process, keeping both teams aligned and focused on moving the deal forward.
Customer Success
1/ Identifying onboarding and workspace setup workflow
Once a deal is closed, it’s important to celebrate success. But it’s not the end! Post-sales activities, like customer success and onboarding, are as important as closing the customer.
The first critical step in our onboarding process was to thoroughly understand the customer's current workflow as if we were joining their team.
We asked for a workflow meeting to map out their sales flow and draft a detailed plan for the Relate implementation.
With this detailed understanding, we effectively planned how Relate would be used within their organization. We determined the necessary configurations and outlined how to integrate Relate with their existing tools.
This preparation ensured a smooth transition and optimal use of our solution within the customer’s organization.
2/ Data migration and setup
The customer had data scattered across multiple spreadsheet files, each with unique data types and management methods. Our task was to consolidate it into a single file and determine how to manage it in Relate.
During this process, we reviewed each data set, providing detailed explanations and demonstrations of how the data would be handled in Relate.
This ensured a smooth transition to Relate.
3/ Onboarding & training
We implemented a segmented approach to onboarding and training, with diverse users and multiple teams adopting Relate (40+ people). We began with an admin-focused session to ensure successful data migration and workspace setup, gathering feedback for improvements.
We organized tailored onboarding meetings for each user group, providing comprehensive guidance on Relate usage.
We focused on integrating Relate into each group's workflow, going beyond mere feature demonstrations.
This method allowed us to introduce features contextually, ensuring users understood how Relate would enhance their work processes.
4/ Follow-up meetings & training sessions
We adopted a strategic approach, recognizing that one onboarding session isn’t enough for complete product mastery and lengthy meetings can be counterproductive.
During the initial onboarding, we focused on essential elements, then scheduled follow-up meetings and training sessions every two to four weeks.
During follow-up sessions, we addressed user questions from their hands-on experience with Relate. We introducedadditional features and guided users through new functionalities for continuous learning and optimal platform use.
Conclusion
Almost a year after their Relate adoption, this customer still uses it daily with their 40+ people and 15k+ organization records in their workspace.
Enterprise sales can be challenging and takes months to discover prospects and their needs, multiple calls and demos, and to arrange onboarding sessions and training programs for the users, but it pays off.
Our journey closing our first five-figure deal demonstrates key insights:
Persistence in outreach is crucial. It took nearly a year of multi-threaded efforts to secure the first meeting.
Thorough research and personalization are essential in understanding and addressing the specific needs of enterprise clients.
Flexibility and responsiveness during the sales process can make the difference in closing a deal, including accommodating new requirements and comparing competitors.
Having a strong internal champion is invaluable for navigating decision-making in a large organization.
A well-executed onboarding process, including tailored training and ongoing support, is critical for long-term customer satisfaction and retention.
By following these principles and maintaining a customer-centric approach, we were able to close our first five-figure deal and lay the groundwork for a long-term relationship with an enterprise client.
We repeated a similar structure/process for the next few deals and we successfully closed several more deals.
Relate started as a product for startups and small businesses. Realizing that moving up in the market accelerates product development and generates revenue quickly, we decided to also build for enterprise customers too.
Today we have several enterprise customers paying five-figure subscription fees. It all started with closing one customer we reached out to as part of our outbound campaign.
Here’s a case study on the Relate team’s first enterprise deal. It details the process from prospecting to closing the deal and onboarding.
Prospecting
1/ Multi-threading: A year-long journey to book the first meeting
Our engagement with this customer exemplifies the persistence and strategic approach required in enterprise sales.
It started when we saw a job posting for a B2B sales representative at the company.
This was a key indicator. Hiring for such a role typically signals current sales success or strategic growth.
We saw an opportunity to introduce our CRM product, so we reached out to the contact to initiate the process.
Our first cold email didn't get a reply, as with any good story.
A few months later, we connected with another executive through our marketing channels (e.g., blog posts, newsletters, etc.).
We reached out to both of them again, at the same time, in separate threads. One for the existing contact, the other for the executive we found.
This is what salespeople call “multi-threading,” a strategy to find the right decision-maker quickly.
When this attempt also went unanswered, we followed up three months later.
We made sure this was shown as persistence, not intrusive or annoying (check out our best practices on cold mailing).
The breakthrough came a year later when the company’s marketing lead signed up for a demo (inbound).
We couldn’t book a meeting immediately, but we followed up for two months, seeking an introduction to the right decision maker and asking for a demo.
Turns out, they were looking for a CRM. We succeeded by sending them messages about how we can help with CRM implementations and migration.
This allowed us to position our solution in their impending CRM implementation, ensuring consideration alongside other tools.
2/ Initial discovery call & product demo
Before our first meeting, we thoroughly researched them, digging up information such as:
Company and service info
Investment history and present status
Customer volume and types from relevant articles
Info on meeting participants from the company blog and LinkedIn
During the meeting, we gained valuable insights:
The company’s organizational structure, especially how sales and marketing collaborate.
Business problems solved through CRM implementation
Prioritizing requirements
Their decision-making process and timeline
We identified three critical pain points this company needed to solve:
Centralizing customer data on a single platform
Managing the entire sales process from lead generation to sales and customer success.
Supporting user adoption of a new tool and process through simple UI/UX and robust support with personalized onboarding and training for a smooth CRM implementation.
Our product demo was concise and targeted, addressing three key priorities.
The approach resonated well with them. They said our solution seemed to be the ideal fit.
Closing the deal
Our champion said our CRM was better than Salesforce, HubSpot, and Pipedrive, so we expected a quick closing. We expected them to move forward within a month.
But the deal didn’t close right away. After a few days of going dark (obviously we followed up religiously), the customer came back and told us they wanted to introduce a new alternative and compare it with Relate.
They presented additional requirements that extended the sales cycle and required more work to win the deal.
1/ Helping champions convince stakeholders
Over a month, we exchanged over 40 emails, mostly with the champion.
They shared with us how internal discussions are going, and we discussed how they can address internal objections. The champion circulated our references and persuaded their team.
During this process, we prepared well-written business case documents, action plans, product demo recordings, and any resource our champion needed.
Having a champion as our proxy was invaluable in navigating the decision-making process, since we couldn’t sit in on every single discussion meeting held internally.
2/ More discovery calls and product demos to understand requirements and priorities
To win this deal, we had to persuade not only the sales department but also marketing and customer support teams. Inenterprise sales, it’s often multiple departments involved in the decision-making process.
We asked our champion to arrange meetings with cross-functional departments for deeper insights into their needs and challenges. During the meeting, we addressed their concerns and tried to tailor our demos to their needs.
After the meetings, we helped the customer prioritize sales, marketing, and customer support requirements and align on areas needing further feature development. We actively participated instead of waiting for their decisions.
Enterprise customers often want custom features and integrations. It’s crucial to show that you can deliver some of these requests and how quickly.
This helped us stand out from other alternatives.
3/ Use a mutual action plan to manage communication.
Since the first discovery call, we had more meetings, emails, and hundreds of Slack conversations. Needless to say, the deal was not done!
This called for a centralized, accessible source of truth for all resources and the project timeline.
To address this, we created a shared workspace for a Mutual Action Plan (using Coda). This document summarized our discussions and decisions, outlined specifications and development timelines for features needing further work, and detailed our onboarding requirements and schedule. This approach ensured clear communication throughout the sales process, keeping both teams aligned and focused on moving the deal forward.
Customer Success
1/ Identifying onboarding and workspace setup workflow
Once a deal is closed, it’s important to celebrate success. But it’s not the end! Post-sales activities, like customer success and onboarding, are as important as closing the customer.
The first critical step in our onboarding process was to thoroughly understand the customer's current workflow as if we were joining their team.
We asked for a workflow meeting to map out their sales flow and draft a detailed plan for the Relate implementation.
With this detailed understanding, we effectively planned how Relate would be used within their organization. We determined the necessary configurations and outlined how to integrate Relate with their existing tools.
This preparation ensured a smooth transition and optimal use of our solution within the customer’s organization.
2/ Data migration and setup
The customer had data scattered across multiple spreadsheet files, each with unique data types and management methods. Our task was to consolidate it into a single file and determine how to manage it in Relate.
During this process, we reviewed each data set, providing detailed explanations and demonstrations of how the data would be handled in Relate.
This ensured a smooth transition to Relate.
3/ Onboarding & training
We implemented a segmented approach to onboarding and training, with diverse users and multiple teams adopting Relate (40+ people). We began with an admin-focused session to ensure successful data migration and workspace setup, gathering feedback for improvements.
We organized tailored onboarding meetings for each user group, providing comprehensive guidance on Relate usage.
We focused on integrating Relate into each group's workflow, going beyond mere feature demonstrations.
This method allowed us to introduce features contextually, ensuring users understood how Relate would enhance their work processes.
4/ Follow-up meetings & training sessions
We adopted a strategic approach, recognizing that one onboarding session isn’t enough for complete product mastery and lengthy meetings can be counterproductive.
During the initial onboarding, we focused on essential elements, then scheduled follow-up meetings and training sessions every two to four weeks.
During follow-up sessions, we addressed user questions from their hands-on experience with Relate. We introducedadditional features and guided users through new functionalities for continuous learning and optimal platform use.
Conclusion
Almost a year after their Relate adoption, this customer still uses it daily with their 40+ people and 15k+ organization records in their workspace.
Enterprise sales can be challenging and takes months to discover prospects and their needs, multiple calls and demos, and to arrange onboarding sessions and training programs for the users, but it pays off.
Our journey closing our first five-figure deal demonstrates key insights:
Persistence in outreach is crucial. It took nearly a year of multi-threaded efforts to secure the first meeting.
Thorough research and personalization are essential in understanding and addressing the specific needs of enterprise clients.
Flexibility and responsiveness during the sales process can make the difference in closing a deal, including accommodating new requirements and comparing competitors.
Having a strong internal champion is invaluable for navigating decision-making in a large organization.
A well-executed onboarding process, including tailored training and ongoing support, is critical for long-term customer satisfaction and retention.
By following these principles and maintaining a customer-centric approach, we were able to close our first five-figure deal and lay the groundwork for a long-term relationship with an enterprise client.
We repeated a similar structure/process for the next few deals and we successfully closed several more deals.
Continue reading
When can startups start selling to enterprise companies? - Ch. 5
How Relate closed the first five-figure deal through outbound sales - Ch. 6
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