Choosing the right email marketing agency can make or break your retention strategy. The best agencies don’t just send emails, they drive revenue, build customer relationships, and refine your strategy over time. But with so many agencies claiming to be experts, how can you tell who actually knows their stuff?
The key is asking the right questions. A great agency will welcome deep, strategic discussions, while a weaker one might stumble over basic concepts or rely on generic, one-size-fits-all approaches.
Before you sign on with an email partner, use these 12 must-ask questions to separate the real experts from the pretenders—and ensure you’re choosing an agency that will deliver results.
1. How do you monitor and improve deliverability over time? How do you handle domain reputation issues?
Why this matters:
Strong deliverability isn’t just about setting up DKIM, SPF, and DMARC. It’s an ongoing process that requires monitoring inbox placement, domain reputation, and engagement trends, and then adjusting sending strategies accordingly. A great agency will take a proactive approach, continuously testing and refining to maintain optimal performance.
Keywords to listen for:
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Inbox placement tracking
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Dedicated IP vs. shared IP considerations
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Spam trap monitoring
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Email authentication & protocol compliance
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Third-party deliverability monitoring tools (i.e. Litmus, Email on Acid)
Red flag phrases to watch out for:
🚩 “We just check Klaviyo’s reporting.” → Klaviyo provides valuable insights, but it doesn’t track inbox placement or spam filtering.
🚩 “As long as you’re not on a blacklist, you’re fine.” → Deliverability issues often occur before blacklisting. Proactive monitoring is key.
🚩 “Open rates tell us everything we need to know.” → Opens can be misleading due to Apple Mail Privacy Protection (MPP) and image caching.
🚩 “We send to everyone to maximize reach.” → This is dangerous and can have detrimental implications on your sender reputation.
2. What’s your stance on image-based emails?
Why this matters:
If an agency is OK with running 100% image-based emails, they’re not following best practices. Image-heavy emails often struggle with deliverability, accessibility, and engagement. Plus, many inboxes block images by default, and text-based content is critical for inbox placement. Look for an agency that understands how to balance visuals with live text for optimal performance.
Keywords to listen for:
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Live text
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Text-to-image ratio
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Inbox placement
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Alt text
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Load speed & mobile optimization
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Dark mode considerations
Red flag phrases to watch out for:
🚩 “It looks better as an image.” or “It’s easier and faster to set up with images.” → At the cost of inbox placement and accessibility?
🚩 “Most email platforms load images by default now.” → Not true. Gmail and Outlook still block images in many cases.
🚩“Branding is the most important thing.” → Branding is important, but not at the expense of deliverability and usability.
🚩“We can just add all the text into the image.” → That means no searchable text, poor accessibility, and deliverability risks.
3. How do you report on success? What metrics do you focus on?
Why this matters:
If an agency’s success metrics are all about vanity metrics (open and click rates), that’s a red flag. While these are useful diagnostic tools, they don’t directly measure business impact. A strong agency prioritizes revenue-based KPIs that reflect email’s role in customer retention, lifecycle engagement, and long term profitability.
Keywords to listen for:
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Conversion rate
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Revenue per recipient (RPR)
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Repeat purchase rate
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Customer lifetime value (LTV)
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Attribution modeling
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Flow vs. campaign performance
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Deliverability health metrics
Red flag phrases to watch out for:
🚩 “We track opens and clicks to gauge performance.” → And then what? What’s the impact on revenue?
🚩 “Engagement rates are the most important metric.” → Engagement matters, but revenue is king.
🚩 “We look at total email revenue.” → Total revenue is meaningless without context. How is email actually performing per recipient, per campaign, per flow?
🚩 “Attribution is tricky, so we don’t focus on it much.” → Email drives revenue in direct and indirect ways, and strong agencies analyze both.
4. If we kicked off today, how soon would you expect new flows to be live?
Why this matters:
If an agency tells you they’ll have flows live in a week or two or promises to launch everything in a quick sprint, they’re likely taking a cookie-cutter, templatized approach. A great agency will dedicate the first phase to due diligence. This includes digging into your brand, audience, and existing email performance before defining a strategy. Customization takes time, and that’s a good thing.
Keywords to listen for:
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Discovery phase / due diligence
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Customer journey mapping
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Performance analysis of existing emails
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Data-driven strategy development
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Iterative launch approach
Red flag phrases to watch out for:
🚩 “We’ll have everything live in 2 weeks.” → That’s a one-size-fits-all approach, not a strategic one.
🚩 “We use our proven templates.” → Templates can be useful, but they should be customized to your brand and audience.
🚩 “We just follow Klaviyo’s recommended flows.” → Klaviyo’s presets are a great starting point, but they don’t account for your brand’s unique needs.
🚩 “We can launch everything at once.” → A thoughtful agency will prioritize high-impact flows first and refine as they go.
🚩 “You don’t need to be involved much.” → Your input is crucial for creating flows that align with your brand’s voice and customer experience.
5. What would a new and improved Abandoned Checkout flow look like for my brand?
Why this matters:
If an agency gives you a crystal clear, pre-packaged answer, they’re likely taking a one-size-fits-all approach. A strong agency will first analyze your current performance, customer journey, product type, and purchase behavior before recommending a strategy. Look for an agency that asks thoughtful questions before providing answers.
Keywords to listen for:
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Audit of your existing flow performance
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Segmentation strategies
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Personalization based on cart contents
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Incentive strategy
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Multi-channel approach
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Testing & iteration
Red flag phrases to watch out for:
🚩 “We use the same Abandoned Checkout flow for all clients.” → Not every brand should have the same recovery strategy.
🚩 “You just need more reminder emails” → Abandoned Checkout flows should go beyond the “nudge” and leverage segmentation, urgency, and personalization.
🚩 “We always recommend adding a discount.” → Blanket discounts train customers to abandon carts on purpose, so it’s important that discount placement is strategically incorporated.
🚩 “We’ll get it live right away.” → Without reviewing your data first?
6. How do you use AI?
Why this matters:
AI can enhance email marketing when used strategically, but not all AI applications are created equal. Some agencies rely too heavily on AI-generated copy, design, and automation without human oversight, leading to generic, off brand messaging. A strong agency will use AI to augment, not replace, expert driven strategy, creative, and personalization.
Keywords to listen for:
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AI-powered segmentation & predictive analytics
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Content ideation & brainstorming
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Coding support and testing
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Human + AI collaboration
Red flag phrases to watch out for:
🚩 “We use AI to generate all email copy and creative.” → AI should assist, not replace expert expert-driven storytelling and brand voice.
🚩 “Our AI automates all decision making.” → Great email marketing still requires human strategy and insights.
🚩 “We let AI handle testing and optimization entirely.” → AI is a tool, but ongoing human oversight ensures strategic adjustments.
🚩 “AI removes the need for manual segmentation.” → AI can enhance segmentation, but human strategy is essential for nuance and brand fit.
🚩 “We don’t use AI at all.” → A modern agency should be exploring AI tools to improve efficiency and performance.
7. Are your copywriters and designers dedicated to email, or do they support multiple channels?
Why this matters:
An email specialized creative team means they live and breathe email strategy, understanding the nuances of deliverability, inbox rendering, conversion copy, and behavioral triggers. If an agency’s creatives are spread across multiple disciplines (social, web, paid media, etc.), email is likely not their primary expertise. Email has unique technical, strategic, and performance considerations that generalist marketers may not fully grasp.
Working within an expert strategic framework, email copywriters and designers seamlessly integrate a brand’s voice and aesthetics into every campaign and flow message. They ensure tone, messaging, and visuals align perfectly with existing branding—creating emails that feel like a natural extension of the brand while driving engagement and conversions.
Keywords to listen for:
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Email-first creative team
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Deep understanding of email deliverability
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Testing for inbox rendering & dark mode
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Experience with Klaviyo, technical constraints, and segmentation-informed messaging
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Expert brand integration
Red flag phrases to watch out for:
🚩 “Our copywriters and designers work across all marketing channels.” → Email requires specialized expertise. If they do everything, they likely don’t excel at email.
🚩 “We repurpose website or ad copy for emails.” → Email copy needs to be tailored for engagement, brevity, and inbox behavior.
🚩 “We primarily focus on brand aesthetics.” → Strong branding is important, but email must also be functional, optimized for deliverability, and focused on conversion.
🚩 “Our team is flexible, so they work across email, social, and paid.” → If they’re stretched thin, email isn’t getting the attention it deserves.
🚩 “We design first, then figure out copy.” → Email should be led by strategy first.
8. Are your copywriters and designers in-house or outsourced? And are they US-based?
Why this matters:
Outsourced teams can lead to inconsistencies in brand voice, slower turnaround times, and communication barriers. Agencies with in-house, US-based talent tend to provide higher quality work, faster execution, and a deeper understanding of your brand over time. When creatives are embedded within the agency, they gain familiarity with your voice, tone, and customer base, leading to more cohesive, on-brand messaging in every email.
Keywords to listen for:
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In-house creative team
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Consistent team members on your account
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Senior-level talent
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Dedicated email copywriters & designers
Red flag phrases to watch out for:
🚩 “We have a network of freelancers we tap into.” → Inconsistent quality, slower turnaround times, low budget.
🚩 “We outsource creative.” → This is often a financial decision, and how many agencies keep costs low. Lower costs often mean lower quality and lack of brand familiarity.
🚩 “Our designers and writers work across multiple marketing channels.” → Email expertise matters. Email-specific creatives understand the channel and all of its nuances better than generalists.
🚩 “We don’t handle creative; you’ll need to provide that.” → If you want full service email marketing, you shouldn’t have to outsource your own creative.
🚩 “We have a global team of creatives.” → That could mean timezone challenges, misaligned messaging, and inconsistent quality.
9. What’s your average client lifespan?
Why this matters:
If an agency struggles to retain clients, it’s often a sign of lackluster results, poor communication, or operational inefficiencies. A strong agency should be able to point to multiple long-term client relationships as proof of their effectiveness, reliability, and ability to drive sustained growth. If most clients leave after just a few months, it’s a red flag that the agency may overpromise and underdeliver.
Keywords to listen for:
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Multi-year client relationships
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Clients who scale their engagement over time
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Low churn rate
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Case studies featuring long-term results
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Opportunity for strategic evolution over time
Red flag phrases to watch out for:
🚩 “Most of our engagements are short-term.” → Why aren’t clients sticking around?
🚩 “We focus on project-based work.” → One-off projects can be useful, but long-term partnerships signal deeper expertise.
🚩 “We work with a high volume of brands.” → Churn and volume-based work can mean less strategic attention for each client.
🚩 “We don’t track client retention.” → If they don’t measure it, they probably don’t prioritize it.
🚩 “We have a lot of turnover, but that’s common in this industry.” → It’s not. Great agencies keep clients for years.
10. What’s the average tenure of your team members?
Why this matters:
A high-turnover agency means your account will constantly be handed off to new strategists, designers, copywriters, and project managers. This leads to inconsistencies in quality, disrupted strategy, and lost institutional knowledge. An agency with long employee tenure suggests stability, deep expertise, and a strong internal culture — all of which benefit your brand in the long run.
Keywords to listen for:
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Low employee turnover
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Team members with years of email-specific experience
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Senior leadership with long tenure
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Dedicated team members assigned to each account for the long term
Red flag phrases to watch out for:
🚩 “We’re always hiring and growing.” → Growth is great, but constant hiring can signal high churn.
🚩 “We have a large team, so there’s always someone available.” → That sounds good, but if people are rotating in and out, your strategy suffers.
🚩 “We have a flexible staffing model.” → That could mean freelancers or short-term contractors handling your account.
🚩 “Your main point of contact might change from time to time.” → Expect turnover, which can disrupt momentum.
🚩 “We prioritize fresh talent.” → Are they investing in employee growth, or just churning through junior hires?
11. Are you a Klaviyo Partner?
Why this matters:
The best answer is “Yes, we are Klaviyo Master Elite Partners.” While there are thousands of Klaviyo Partners, fewer than 30 agencies hold Master Elite status — a designation that reflects deep Klaviyo expertise, a proven track record, and direct access to premium support and resources. Agencies with this status have exclusive insights, early access to new features, and priority support, which can make a huge difference in optimizing your email program.
Keywords to listen for:
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Klaviyo Master Elite Partner
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Direct relationships with Klaviyo’s team
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Experience with advanced Klaviyo features
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Proven Klaviyo track record
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Prioritized Klaviyo support
Red flag phrases to watch out for:
🚩 “Yes, we’re a Klaviyo Partner.” → Anyone can be a partner. Ask what level they are.
🚩 “We use Klaviyo for some of our clients.” → Do they specialize in Klaviyo, or is it just one of many platforms they touch?
🚩 “We’re experienced with multiple ESPs.” → Jack of all trades, master of none? True Klaviyo specialists go deep into the platform.
🚩 “We rely on Klaviyo’s default flows and templates.” → Customization and strategic automation are key. Agencies should go beyond presets.
🚩 “We don’t have a direct Klaviyo contact, but we can submit support tickets.” → Master Elite agencies have priority support channels for faster issue resolution.
12. What kind of engagement options do you offer?
Why this matters:
Many agencies lock clients into long-term contracts, making it difficult to pivot if things aren’t working. If an agency requires a six-month or year-long commitment up front, it could be a sign that they’re more focused on retaining contracts than delivering ongoing value.
A strong agency believes in earning long-term partnerships through results, not contracts. Look for an agency that offers flexibility, transparency, and engagement options that fit your needs (without forcing you into a rigid, long-term commitment).
Keywords to listen for:
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Month-to-month engagement
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Flexible partnership model
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No long-term contracts required
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Custom engagement options
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Ongoing adjustments available
Red flag phrases to watch out for:
🚩 “We require a six-month (or longer) contract.” → Why? Do they need contractual security because clients don’t stay on performance alone?
🚩 “We find that long-term contracts ensure the best results.” → A good agency delivers results no matter the contract length.
🚩 “We have a set engagement model that all clients follow.” → Your business isn’t the same as everyone else’s. Why should your engagement be?
🚩 “We typically review contracts at the end of the year.” → What if things need to change sooner?
🚩 “We don’t offer short-term engagements.” → A strong agency should be confident enough to let results speak for themselves.
Hiring an email marketing agency isn’t just about finding someone who can send emails. It’s about choosing a strategic partner who will help you grow your brand, maximize customer retention, and drive long-term revenue.
By asking these 12 critical questions, you’ll quickly uncover which agencies take a thoughtful, data-driven approach and which ones rely on cookie-cutter solutions. Look for an agency that asks questions before giving answers, prioritizes strategy over shortcuts, and continuously optimizes for better results.
The right partner will feel like an extension of your team, not just a vendor. They’ll bring fresh insights, push your strategy forward, and work alongside you to make email a high-performing revenue channel.
Ready to work with an agency that checks all the right boxes? Book a call with our email marketing experts.
