Chili Piper vs. Wingman (legacy product)

Chili Piper is GREAT for sales development teams booking for sales people. This is especially true when there is a "round robin" system that needs to be abided by. I've experienced a lot of bad round robin systems and Chili Piper's is fantastic. This is also a great tool to schedule with people across multiple time zones, which I don't want to have to focus on while speaking. It enables sales reps to focus on the prospect, not the time change. Chili piper would not be a good fit for underperforming sales teams that don't book any meetings (:

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Wingman would be well suited for any organisation with more than 5+ reps in their sales team. Recording all the demo calls will create a playbook which will help the reps learn from each other and also to ramp up new reps with how to conduct the demo and discovery calls

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• Chili Piper integrates with Salesforce very well which I haven't seen other calendar apps do yet.
• Meeting Buffer functionality assures that AEs won't be booked back-to back.
• I can send the link to each of my meeting templates for different prospects

• Filtering calls by keywords - saves you time so that you don't have to listen to entire calls.
• Creating game tapes - so that you can easily onboard new team members.
• Great support team (love for Sushma).
• Much cheaper than competitors.

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• They are continually improving their offering and we've seen great leaps over the past 2 years.
• Would be nice to be able to modify the email reminders for every single contact and event versus have set templates
• Faster load times, but we can’t complain too much!

• Searching for specific calls (you can scroll through the list, but that takes time)
• The dashboard isn't as user friendly as it could be, but a seasoned user can navigate it just fine
• The AI-driven insights aren't always accurate but are still very useful nonetheless

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I think Wingman is one of the best software in their segment. Very few companies are cost-effective and offer similar solutions.

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Super user friendly tool! There are some features that I think might be improved over time, like navigation assistance or tutorials, and quick tips, like how to ensure calls always get recorded, how to add Wingman to calls last-minute, or how to use their playlist feature Game Tapes, but those are nice to haves, not need to haves.

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• Support was very responsive during our integration phase, and after that too.
• They have the whole infrastructure built to notify customers about bug/outages, which is excellent. Entire System outage only happened once, but being updated on fix progress helped a lot to keep our team calm.

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Wingman is always quick and thorough with their support and often offer to proactively connect on Zoom. I love that.

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I wasn't directly involved but no news is good news in our organization for topics like this!

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Calendly was being used at the company by some other departments and still is to some extent. However adding Chili Piper fore the marketing and sales departments was a no brainer once we saw the demo. It's Calendly on steroids and the company is just getting started using it. I'm sure we will see even more benefits as the years go on.

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Gong is expensive but it has a lot better AI/Intelligence feature compared to Wingman. Wingman definitely does the job, is cheap, and also support is pretty amazing and I personally like Shruti a lot in terms of what she is doing in this space. Also, Wingman is in an Indian company.

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• More demos held by simplifying the scheduling process. More demos = more opportunities
• Initial set up was frustrating and created a lot of mix up which allowed some leads to slip through the cracks early
• Integration with Salesforce.com saved our reps time because they didn't have to log activities manually

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• Training of new Sales representatives has gone from 1 month to 2 weeks using Wingman as part of the training tools.
• The transcripts have also helped us to decrease the number of disputes "Lost" on Stripe, by providing evidence needed to win the case.

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Independently Invited by TrustRadius

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