Latest / Sidekick's What Just Shipped / HubSpot Breeze writes your Gmail replies from CRM data | Shipped Aug 2026
Transcript
- Rob (AI host): A prospect replies asking about next steps, and the deal details you need are sitting in HubSpot, one tab away from Gmail. Dana (AI host): Breeze Assistant can now draft that reply right inside Gmail, using the thread and your CRM data. Rob (AI host): It writes the draft, you shape it, and nothing leaves your outbox until you hit send. Narrator (AI voice): This is Sidekick's What Just Shipped, presented by Sidekick Strategies. Narrator (AI voice): Your hosts, Rob and Dana, are AI. Narrator (AI voice): The voices are synthetic, the research is real, and humans check every claim before it reaches you. Rob (AI host): A disclosure: Dana and I are AI hosts, and neither of us has a Gmail inbox. Rob (AI host): We're working from HubSpot's help article on writing Gmail emails with Breeze, updated September tenth, 2026. Dana (AI host): And today I'm playing a sales rep who lives in Gmail and opens HubSpot only when someone makes me. Rob (AI host): Perfect. Here's what's new. Rob (AI host): In the HubSpot Sales Chrome extension, Breeze Assistant can generate and refine emails in Gmail, using your CRM data and the current email thread. Dana (AI host): What does "CRM data" mean in my world? Rob (AI host): HubSpot says Breeze can surface relevant contact, deal, and activity information, then use that context to write personalized email content. Dana (AI host): Give me the moment I'd use it. Rob (AI host): HubSpot's own example: a contact replies asking about next steps for an open deal. Rob (AI host): Breeze drafts the response from the email thread, the deal details, and recent activity in HubSpot. Dana (AI host): Okay, that's my Tuesday. Is this a Sales Hub Enterprise thing? Rob (AI host): No. HubSpot lists it for all products and plans. Dana (AI host): Then what do I need set up first? Rob (AI host): Three things. Install the HubSpot Sales Chrome extension. Rob (AI host): Have an admin turn on Give users access to Breeze Assistant in your AI settings. Rob (AI host): And you need personal email access to send emails through the extension. Dana (AI host): That second one isn't mine to flip. I'd have to ask an admin. Rob (AI host): Right, that's an admin setting. Rob (AI host): And HubSpot adds a tip for admins: set up your brand kit so the drafts sound like your business and your brand voice. Dana (AI host): What's a brand kit, for a rep who's never opened one? Rob (AI host): It's where your company describes its business and brand voice, so HubSpot's AI tools write the way your team writes. Rob (AI host): HubSpot links to a guide on teaching its AI tools about your business. Dana (AI host): Okay, I'm set up. Walk me through it. Rob (AI host): In Gmail, open an existing email or click Compose. Rob (AI host): In the compose toolbar, click Write with Breeze. Dana (AI host): And then? Rob (AI host): The HubSpot Sales panel opens with a generated draft. Read it. Rob (AI host): If it's off, type more prompts to refine it, like "shorter" or "mention the pricing call." Dana (AI host): Can it help with a brand-new email, or only replies? Rob (AI host): Both. Rob (AI host): HubSpot's steps start with either an existing email or Compose, so you can begin from a blank message. Rob (AI host): On a reply, the thread gives it more to work with. Dana (AI host): Does it just send? Rob (AI host): No. You click Insert to drop the draft into the Gmail composer. Rob (AI host): Then you edit it however you want, and you send it yourself. Dana (AI host): Good. I'm not letting anything send in my name without me reading it. Rob (AI host): That's how HubSpot built it: generate, refine, insert, edit, then send. Dana (AI host): What about privacy? My prospects' emails are going into this. Rob (AI host): HubSpot says admins manage AI feature access in AI settings and choose what data is shared. Rob (AI host): They point to their AI Trust FAQs and AI Model Cards for security, data use, and compliance details. Rob (AI host): If your company has rules about AI, that's where your admin should start. Dana (AI host): And if my admin never turned it on? Rob (AI host): Then Write with Breeze won't work for you. Rob (AI host): The AI settings switch comes first, so that's the first message to send your admin. Dana (AI host): Why it matters: the best context for a reply now comes to the inbox, instead of the rep going to find it. Rob (AI host): Our research puts it this way: the best AI tool is the one that shows up where people already work. Dana (AI host): Who should try it first? Rob (AI host): Our research points to sales reps and BDRs who send a lot of personal outreach from Gmail, founders who write their own follow-ups, and enablement leads who'll roll it out. George B. Thomas (AI voice clone): Hey, it's George B. Thomas from Sidekick Strategies. George B. Thomas (AI voice clone): Full honesty, this is my AI voice clone, made with my permission. George B. Thomas (AI voice clone): AI drafts help most when the sales process underneath them is clear. George B. Thomas (AI voice clone): Our Sales Hub implementation starts by interviewing your reps, managers, and ops team, then builds your deal pipeline, sequences, playbooks, meeting links, and quote templates around how your team actually sells. George B. Thomas (AI voice clone): Learn more under services at Sidekick Strategies dot com. Dana (AI host): Rob, you said the button changed. What's different from our write-up? Rob (AI host): Our write-up from August describes an AI button that opens an "Edit with Breeze" window, with Rewrite, Shorten, Expand, and Change Tone, and a Replace button. Rob (AI host): It also says you need extension version three point one point one or later. Rob (AI host): HubSpot's current help article describes something else: Write with Breeze in the compose toolbar, a draft in the HubSpot Sales panel, prompts to refine, and an Insert button. Rob (AI host): We couldn't find the four editing actions, the Replace button, or a version number on any HubSpot page, so follow HubSpot's steps. Dana (AI host): And the claim that every email logs back to HubSpot? Rob (AI host): That's about how your extension's logging is set up, not this feature. Rob (AI host): HubSpot's article on Breeze in Gmail doesn't mention logging, so check your own settings. Dana (AI host): Then give me a plan, for the rep who lives in Gmail all day long. Rob (AI host): Step one: ask your admin whether Breeze Assistant is turned on in AI settings, and whether the brand kit is filled in. Dana (AI host): Step two: open Chrome's extensions page and make sure HubSpot Sales is installed and up to date. Rob (AI host): Step three: pick one real reply from today, ideally a prospect asking about next steps on an open deal, and click Write with Breeze. Dana (AI host): Step four: refine with one or two prompts, click Insert, then read every line before sending. Dana (AI host): Check names, numbers, and dates against the record. Dana (AI host): And if the draft gets a deal detail wrong? Rob (AI host): Fix it in Gmail before you send. Rob (AI host): Once you click Insert, it's your draft, and HubSpot's own steps say to edit the content as needed. Rob (AI host): Step five: after a week, compare a handful of Breeze drafts with your own. Rob (AI host): Keep the prompts that worked best and share them with the rest of the team. Dana (AI host): My Gmail rep is sold. Dana (AI host): It's one less tab to open, the context comes to me, and I'm still the one who hits send. Rob (AI host): Bottom line: Write with Breeze, then Insert, then you edit and send. Dana (AI host): Our sources are linked in the show notes, and there's more of our research at Sidekick Strategies dot com. Rob (AI host): Thanks for letting us into your inbox today. Dana (AI host): Draft fast, send human. Narrator (AI voice): Sidekick's What Just Shipped is presented by Sidekick Strategies, with AI hosts Rob and Dana and AI-generated music. Narrator (AI voice): We're independent, and not affiliated with HubSpot. Find our research at Sidekick Strategies dot com.