How Gladly Deployed AI for Presales Automation
The Challenge
Gladly has a stellar reputation for delivering the best customer service and they’re growing fast. With that growth comes a steep rise in customer questions, RFPs, and security questionnaires. These complex and lengthy documents can be full of technical questions that can take hours to manually complete. Gladly needed a more efficient, scalable way to automate the questionnaire completion process.
The Outcome
1up helped Gladly automate answers using technical documentation. By unifying the company’s product docs and sales assets, Gladly is able to generate automated RFP responses and complete technical questionnaires in minutes. From a 200-question RFP to a single query from a customer, 1up enables Gladly’s teams to accelerate sales cycles.

When Explosive Growth Brings an Influx of Questionnaires
Gladly is a leading customer service AI platform serving huge brands like Nordstrom, Warby Parker, Crate & Barrel, and Tory Burch. They do it with a brilliant support suite that unifies customer interactions across channels.
Rave reviews and a fast-moving product team led to Gladly achieving high growth while keeping headcount efficient.
That’s when the sales questionnaires started to spike up. With so many new customers in the mix, Gladly was seeing a high volume of RFPs, security reviews, and due diligence questionnaires.
Gadly’s Account Executives and Solutions Engineers needed in-depth product knowledge to answer tough technical questions from customers. And, with more conversations with prospects, and a growing queue of questionnaires to fill out, the sales team just didn’t have the time, creating bottlenecks in the sales process.
They Had Great Documentation. They Just Needed to Automate
Gladly has tons of great documentation across their website and internal documents. And let’s not forget the hundreds of previously completed questionnaire responses.
The team had a gold mine of knowledge. But finding answers quickly is a whole other story. Their ability to search their knowledge bases quickly was limited. The SE team tried investing in a tool to organize their content library, but found themselves spending just as much time managing the knowledge base.
They needed a way to connect separate knowledge sources into a single platform that was easily accessible to their entire team and would do the job of automating hundreds of answers to complex questionnaires.
That’s where 1up comes in.
Automating Answers with 1up
1up brought a fast, AI-native approach to unifying Gladly’s documentation. Now they’re able to generate responses to long questionnaires and one-off customer questions.
1up connected all of Gladly’s most commonly used knowledge sources:
- Product documentation
- Sales assets
- Website
With this mix of sales and technical docs powering AI Knowledge Management, the Gladly team can quickly, accurately, and precisely respond to two kinds of queries:
- Complex RFPs and compliance questionnaires: When potential clients send over an RFP or security questionnaire, the sales team can simply upload it to 1up. 1up generates answers from Gladly’s centralized knowledge base, completing the questionnaire in a matter of minutes.
- One-off questions in Slack: When a team member has a question about product knowledge, sales, or anything else, they can just message @1up in Slack. In seconds, 1up will respond with the right answer straight from company files.
It’s like having the hardest working intern who’s available 24/7, knows everything about your company, and can answer questions and questionnaires FAST.

Automating Knowledge by Extending 1up to Slack
And while 1up saved the Gladly team time, energy, and money, one of their favorite features is the ability to automate company knowledge in Slack.
Now members of the Sales and Solutions teams can jump into Slack and ask @1up for fast answers to technical questions.
No more manual searches. No more bothering teammates. Everyone has easy access to the same product knowledge.
Gladly was even able to specify which answer sources can be used in Slack and which channels 1up can respond in. This gives the team full control over how and where 1up will respond.
Because 1up is locked into Gladly’s knowledge sources and limited to only retrieving answers from within, the team never has to worry about inaccuracies or hallucinations.
The Impact
- RFPs and questionnaires get done in minutes, not days or weeks.
- Sales reps can ask any technical question without distracting teammates.
- The Sales and Solutions teams can get answers to any technical question in seconds.
Most importantly, Gladly no longer has to interrupt work by searching for knowledge. They can focus entirely on driving customer success.
1up was able to transform the entire sales process for the team at Gladly with quick response times, a centralized sales knowledge base, and easy collaboration tools.
1up has become an invaluable tool for Gladly, and we are so excited for the entire team’s success.
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