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Co-Founder & Strategic Systems Director
Aaron's a systems thinker who builds marketing engines that perform. He leads the team at Triple Take with a strategic mind and an eye for what works.
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Co-Founder & Creative Director
Jason's a creative visionary who knows how to spot the story that makes a business stand out. He leads the team with a sharp eye and high standards.
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Marketing Project Manager
Madison is the reason Triple Take campaigns launch flawlessly and on schedule. She's part project manager, part mind reader, and part miracle worker.
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Jonathan makes local businesses look like industry leaders through his camera lens. He captures the authentic moments that make your customers think "I want to work with these people."
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Julia is a master at creating authentic-looking content that converts. She specializes in creating ads that feels genuine—like a real customer sharing their experience.
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We work with businesses of all sizes, from local startups to established companies. Whether you’re seeking digital strategy, advertising, content creation, or SEO services, we tailor our approach to meet your specific goals and industry needs.
At Triple Take, we prioritize building genuine partnerships with our clients. This means taking the time to understand your business, audience, and objectives. From there, we craft creative solutions that align with your vision and deliver measurable results.
We put people first. With an on-call mentality, we’re always here for you. If something isn’t working, we fix it—fast. We’re not just a service provider; we’re your partner.
If you're running cold email campaigns for your business, you've likely asked yourself this critical question: "Which platform will give my emails the best chance of actually reaching my prospects' inboxes?"
It's a question worth asking. After all, even the most brilliantly crafted cold email is worthless if it lands in the spam folder.
At Triple Take Marketing, we've helped countless businesses optimize their cold email strategies, and one of the most common dilemmas we see is the choice between Google Workspace (Gmail with a custom domain) and Microsoft 365 (Outlook with a custom domain).
Today, we're settling the debate with a data-driven comparison specifically focused on businesses sending moderate volumes (70-100 emails per day) using automation tools like Woodpecker.
Let's start by addressing what doesn't matter much in this comparison:
Technical sending limits aren't a significant factor for most businesses sending 70-100 cold emails daily:
Google Workspace allows up to 2,000 emails per day
Microsoft 365 permits up to 10,000 recipients daily (with a rate limit of 30 messages per minute)
Both platforms offer more than enough capacity for moderate-volume campaigns. The real differences lie elsewhere.
Before diving into the differences, it's important to understand that both Gmail and Outlook demand certain fundamentals for successful cold email delivery:
Meticulous account warm-up - Gradually increasing sending volume over weeks
Proper technical setup - SPF, DKIM, and DMARC authentication
Quality content and lists - Non-spammy messaging and verified recipient addresses
Engagement monitoring - Tracking opens, clicks, and replies
Clear unsubscribe options - Maintaining compliance and sender reputation
No platform offers shortcuts around these essentials. Neglect them, and you'll struggle with deliverability regardless of which service you choose.
Here's where things get interesting—and where the real differences between Gmail and Outlook emerge for cold emailers.
The Good:
More predictable filtering behavior when following best practices
Generally more forgiving of cold outreach when properly executed
More consistent deliverability patterns reported by users
Better tolerance for gradual scaling when engagement metrics remain positive
The Challenges:
Still requires rigorous adherence to sending best practices
Shared IP reputation can affect deliverability (though custom domains help)
Will still penalize poor content or list quality
The Good:
Professional platform with robust features
High technical sending capacity
Strong integration with other Microsoft products
The Challenges:
More aggressive and less predictable spam filtering for cold outreach
Higher tendency for emails to land in spam/junk folders despite following best practices
Reports of periodic "deliverability crises" affecting Outlook users
More sensitive to patterns associated with cold outreach
Quicker to flag domains or IPs if not managed with extreme care
When using cold email automation tools like Woodpecker (which help with personalization, follow-ups, and sending with human-like delays):
Google Workspace + Woodpecker: With proper warm-up and configuration, sending 70-100 emails/day is typically sustainable with good inbox placement, assuming engagement metrics remain positive.
Microsoft 365 + Woodpecker: While Woodpecker applies the same sending best practices, Microsoft's inherently stricter filtering means there's a higher risk of deliverability issues compared to Google Workspace—even with identical campaign setups and list quality.
Based on extensive research, industry discussions, and user experiences:
Google Workspace (Gmail with custom domain) generally lands in spam less often and offers more consistent deliverability for well-managed cold email outreach at volumes of 70-100 emails per day.
This assessment is supported by:
Fewer reports of sudden, unexplainable deliverability problems from Google Workspace users following best practices
More consistent positive experiences shared by users of cold email tools with Google Workspace
Microsoft 365's reputation for having more stringent and sometimes less transparent spam filtering
Whichever platform you choose, these factors remain critical:
Domain age and history - Newer domains require more extensive warm-up
Content quality - Avoid spammy language and irrelevant messaging
List hygiene - Prevent bounces and avoid spam traps
Engagement metrics - Monitor and optimize for opens and replies
Technical perfection - Ensure flawless authentication setup
Custom tracking domains - Protect your primary domain's reputation
While neither platform guarantees 100% inbox placement for cold emails, Google Workspace emerges as the more favorable option if your primary concern is minimizing spam placement and achieving stable deliverability for cold outreach campaigns of 70-100 emails per day.
Microsoft 365, while excellent for general business email, presents a higher risk of deliverability challenges for cold outreach specifically.
That said, your mileage may vary based on your specific industry, audience, and email practices. The most successful cold email campaigns combine the right platform with meticulous execution and continuous optimization.
At Triple Take Marketing, we specialize in helping businesses achieve breakthrough results with cold email campaigns—regardless of which platform you're using.
Our team can help you:
Set up proper authentication and technical infrastructure
Develop high-converting cold email sequences
Implement proper warm-up and scaling strategies
Monitor and optimize deliverability metrics
Troubleshoot spam issues and improve inbox placement
Don't let your carefully crafted messages get lost in spam folders. Contact Triple Take Marketing today to ensure your cold emails consistently reach their targets and drive real business results.
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