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Email marketing for startups: How to get paying customers using email

Fuel your startup's growth with this actionable email marketing guide. Learn proven strategies to optimize onboarding, nurture trials, maximize customer lifetime value, and win back lost customers.
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Acquiring the first paying customers is a significant milestone. It validates the product or service and provides invaluable feedback for further refinement. Strategic email marketing can expedite this process and set the stage for sustained revenue generation.

In a startup’s crucial early stages, when revenue generation is paramount, email marketing is an indispensable tool for gaining and retaining customers. Email enables direct and personalized communication, fostering more robust customer relationships and driving conversions.

Core email marketing strategies that work for startups

The core email marketing strategies outlined in this guide are designed to target different stages of a customer’s journey with a startup. From initial onboarding to nurturing trial users, from employing lifecycle marketing to offering intelligent upgrades, and finally implementing win-back campaigns, each strategy plays a vital role in acquiring, retaining, and growing customers.

They are not standalone strategies, but interconnected tactics that collectively create a comprehensive and effective email marketing campaign. By understanding and implementing these strategies, startups can fully harness the potential of email marketing to build strong customer relationships, improve user experience, and ultimately drive sustained revenue growth.

This guide outlines five core email marketing strategies to help startups acquire their initial paying customers and foster long-term revenue growth.

1. Optimized Onboarding: Transforming New Users into Confident, Revenue-Generating Customers

The onboarding process is a critical juncture in the customer journey. A well-crafted onboarding experience cultivates a positive initial impression and instills confidence in the product, accelerating the path to generating revenue from these new users.

Email Tactics for Onboarding

Strategic email communication is essential for effective user onboarding. A focused email strategy welcomes new users and guides them toward successful product adoption and engagement. Key tactics include a Welcome Series, Customized Tips, and Check-In Emails.

Welcome Series: Initiate a series of welcome emails triggered upon signup or first login. The initial email should set clear expectations, emphasize the product’s value proposition, and encourage exploration of features that lead to paid conversions. Subsequent emails can delve deeper into specific use cases, offer personalized tips, or provide quick wins to demonstrate immediate value and encourage upgrades to paid plans.

Customized Tips: Segment users based on demographics, interests, or behaviors. Tailor onboarding content to each segment to enhance engagement and guide users toward premium features or services.

Check-In Emails: Proactively reach out to address potential questions or concerns, reinforcing your commitment to customer success and nurturing a relationship that encourages investment in your product.

Try These Subject Line Templates:

  • A Quick Hello and [Product Name] Update
  • Have a Question About [Product Name]? We’re Here to Help!
  • How’s Your Experience with [Product Name]?

Consider the following templates for the email body:

Personalize your greeting – Use the recipient’s name (if you have it) to create a warmer tone. E.g., “Hi [Recipient Name]” or “Hello [Recipient Name]”.

Express your purpose – Clearly state the reason for your email. E.g., “I wanted to check in and see how you’re doing with [Product Name]” or “I’m reaching out to see if you have any questions or feedback about [Product Name]”.

Reference previous Interactions (if applicable) – Include any past conversations or onboarding sessions to add context. E.g., “Since our last conversation about [topic]” or “I hope you’ve had a chance to explore the [feature] we discussed”.

Offer assistance – This is the core of your check-in. Be proactive in providing support. E.g., “Have you encountered any roadblocks or challenges using [Product Name]?” or “We have some new resources/tutorials/features that you might find helpful.” (Provide links or brief descriptions.)

Value reminder (optional) – Highlight a key benefit or feature the customer may not utilize. E.g., “Did you know that [Product Name] can also help you [benefit]?” or “Many of our customers have found success using [Product Name] for [specific use case]”.

Call to Action – Guide the recipient on the next steps. E.g., “Feel free to reply to this email with any questions” or “Would you like a quick [demo/walkthrough/Q&A session]?”.

Sign-Off with a human touch:

Use a friendly and professional closing, such as “Thanks,” “All the best,” or “Sincerely.” Include your name, title, and company information.

Let’s take a look at this email from Musicbed, a platform for licensing music. The Musicbed email excels at customer engagement by effortlessly blending personalization and utility.

“Find Your Music In Seconds,” piques interest with a direct value proposition. Inside, a clear call to action (“Try It Now”) is supported by concise instructions and a “Pro Tip” showcasing the platform’s unique features. This streamlined approach respects the user’s time while effectively communicating the product’s core benefits. The inclusion of navigation options and social media links further enhances user experience, making this email a prime example of effective product communication.

Measuring Onboarding Success for Revenue Impact

Track key metrics such as time to first purchase, customer lifetime value (CLTV), and average order value to evaluate the effectiveness of your onboarding process. By analyzing these metrics, you can pinpoint areas for improvement and optimize your emails to drive revenue generation.

Website Analytics: Utilize tools like Mixpanel or Google Analytics to track interactions on your website or app. This data can reveal how long users can make their first purchase after signing up (time to first purchase) and the average value of their transactions (AOV).

CRM Software: A Customer Relationship Management system helps manage customer data and track purchases over time. By analyzing purchase history, startups can calculate CLTV, the total value a customer generates throughout their engagement with the company.

Subscription Analytics Platforms: For subscription-based businesses, platforms like ChartMogul or Baremetrics track recurring revenue metrics, including CLTV and churn rate. These metrics are crucial for understanding customer lifetime value and retention.

Custom Tracking: Depending on the specific onboarding process and goals, startups can implement custom tracking events or attributes within their analytics tools to capture more granular data related to user behavior and conversions.

A/B Testing: Experiment with different onboarding flows, messaging, or incentives to see which variations improve metrics like time to first purchase and AOV. This data-driven approach can help optimize the onboarding experience for maximum effectiveness.

2. Effective Trial Nurturing: Maximizing Trial Value and Driving Paid Conversions

Free trials are an effective customer acquisition tool, but many trial users fail to convert into paying customers. Strategic trial nurturing through email can bridge this gap by maximizing the value users derive during the trial period and increasing their propensity to subscribe.

Nurturing Emails for Trial Users

Value Emails: Craft a series of emails that showcase the product’s diverse use cases and underscore the financial benefits it delivers to users. Highlight features that address pain points and deliver quantifiable value to the target audience.

Success Stories: Share compelling case studies or customer testimonials demonstrating how your product has helped others achieve tangible financial results.

Progress Updates: Send personalized emails that track users’ progress throughout the trial and emphasize the value they are gaining. This approach can prompt them to consider upgrading to continue experiencing those benefits.

Urgency Emails: As the trial period nears its end, send reminder emails to create a sense of urgency. Offer limited-time discounts, exclusive bonuses, or extended trial periods to incentivize paid conversions.

Shopify’s email exemplifies effective trial nurturing by creating a sense of urgency and emphasizing the benefits of continuing with the platform. The prominent headline, “Your free trial ends tomorrow,” immediately captures the user’s attention and prompts them to take action. 

The email reinforces the value proposition by highlighting key features like selling through various channels, 24/7 customer support, and POS integrations. These features are presented as solutions to common pain points for online businesses, encouraging the user to consider how Shopify can help them achieve their goals. The clear call to action, “Choose a plan,” and the option to “Compare plans” make it easy for users to take the next step and convert to a paying customer.

Measuring the Financial Impact of Trial Nurturing

Monitor the trial-to-paid conversion rate to gauge the success of your trial-nurturing campaigns. Additionally, analyze the following metrics to refine your approach and maximize revenue:

Engagement Rate: Track email open rates, clicks, and time spent on the product to assess user interest and interaction with trial-nurturing communications.

Feature Usage: Identify which features trial users engage with most frequently to understand their preferences and tailor messaging accordingly.

Trial Extension Requests: Monitor the volume of trial extension requests to identify potential customers who require additional time or support to evaluate your product thoroughly.

3. Strategic Lifecycle Marketing: Nurturing Customer Loyalty for Long-Term Revenue Generation

Acquiring customers is just the first step. Retaining them is equally crucial for sustained revenue growth. Strategic lifecycle marketing employs targeted email campaigns to engage customers at different stages, fostering loyalty and maximizing customer lifetime value (CLTV).

Understanding the Customer Lifecycle for Revenue Optimization

Understanding the customer lifecycle is essential for tailoring marketing and sales strategies to optimize revenue at each stage of their journey. Different stages require distinct approaches to maximize customer value and retention.

New Customer: Recently acquired customers exploring the product. Focus on demonstrating immediate value and upselling premium features.

Active User: Regularly engaged customers deriving value. Offer loyalty programs, upsells, and exclusive discounts to maximize revenue.

At-Risk Customer: Users with declining engagement. Re-engage with personalized offers and win-back campaigns.

Inactive Customer: Users who have ceased using the product. Reactivate with targeted offers, showcasing new features or improvements.

Here’s an email structure designed for strategic lifecycle marketing, explicitly targeting at-risk and inactive customers.

Subject Line Options:

For at-risk customers – “Exclusive Offer for Our Valued Customers, [Customer Name]” or “We Miss You, [Customer Name] – Here’s a Special Offer” or “Come Back and Enjoy a Special Discount on Us”

For inactive customers- “[Customer Name], We’ve Added Exciting New Features to [Product Name]” or “Curious About What You’ve Missed? We Have an Update for You”

For the email body, try these approaches:

Personalize greetings and acknowledgement – Use the customer’s name (if possible) to establish a personal connection. Acknowledge their decreased activity or inactivity, but avoid a judgmental tone. E.g.,

  • At-Risk – “Hi [Customer Name], We’ve noticed you haven’t been using [Product Name] as much lately, and we want to make sure everything’s all right.”
  • Inactive – “[Customer Name], we hope everything is well! We wanted to see if we can help you return to using [Product Name].”

Add value reminders and apply a re-engagement strategy

  • At-Risk – Re-emphasize the core value proposition of your product/service. Offer a personalized incentive to re-engage (discount, free trial, or exclusive access.). Suggest specific features or resources they find helpful. E.g., “We know you loved using [Product Name] for [benefit]. We’ve recently added [new feature] that can help you even more with [benefit].”
  • Inactive – Focus on what’s new or improved since they last used the product. Showcase success stories or testimonials from other customers. Offer a solid incentive to return, such as a significant discount or an upgraded feature for free. E.g., “Since you last used [Product Name], we’ve made some major improvements to [features]. We’d love for you to come back and see how it can benefit you now.”

Offer support and guidance – Let them know you can answer questions or provide assistance. Offer resources like tutorials, webinars, or knowledge-based articles. E.g., “Our customer support team is always here to help. Feel free to reach out if you have any questions or need a refresher on how to use [Product Name].”

Add clear Call to Action – Direct them to take a specific action to re-engage with the product. Use a compelling CTA button or link (e.g., “Try the New Feature,” “Claim Your Discount,” “Restart Your Subscription”). Make the action as simple and frictionless as possible.

Sign-Off: End with a warm and friendly tone. Express your hope of seeing them back soon. Include your brand name and contact information.

Let’s examine how Linktree’s email effectively targets new customers by showcasing the enhanced features of their upgraded store. The headline, “New ways to sell more,” immediately appeals to the user’s desire for increased sales. The email then details specific benefits like new layouts, the ability to add product links from anywhere, and the option to mix products from different stores.

Tracking Lifecycle Marketing’s Impact on Revenue

Monitor customer retention rate, repeat purchase rate, and customer lifetime value (CLTV) to gauge the effectiveness of lifecycle marketing and its impact on revenue generation.

Retention Rate: Assess customer retention rate to evaluate the percentage of customers who remain active users of your product or service over a defined period, indicating loyalty and the effectiveness of retention strategies.

Repeat Purchase Rate: Measuring the frequency with which customers make additional purchases after their initial transaction is a practical way to evaluate the effectiveness of strategies to drive repeat business. This metric provides tangible insights into the success of your plan.

Customer Lifetime Value (CLTV): Calculate customer lifetime value (CLTV) to assess the average total revenue attributed to a customer over their relationship with your company. This provides insights into the long-term financial impact of acquiring and retaining customers.

4. Intelligent Upgrades: Generating Additional Revenue through Value-Driven Upsells

Upselling existing customers is a proven method for increasing revenue. Intelligent upgrades utilize email marketing to present upsell opportunities at the optimal time and within the proper context.

Timing is Key: Just-in-Time Emails

Trigger emails can help achieve significant revenue growth by ensuring relevance and maximizing the likelihood of a purchase. By aligning email communication with specific user actions or behaviors, businesses can present relevant upgrade opportunities, increasing conversion potential and driving overall revenue. Startups can utilize several triggers to achieve this goal, including usage-based, feature-focused, and value-driven triggers.

Usage-Based Triggers: Send upgrade emails when users reach specific engagement levels that indicate they derive value and might be open to additional features.

Feature-Focused Triggers: Suggest upgrades that unlock advanced functionalities related to features the user frequently utilizes.

Value-Driven Triggers: Identify pain points or challenges the user is experiencing and present an upgrade that directly addresses those issues. Crafting Effective Upgrade Emails for Revenue Generation

Highlight financial benefits: Clearly articulate how the upgrade will enhance the user’s ROI or deliver cost savings.

Use social proof: Incorporate testimonials from customers who have experienced financial gains after upgrading.

Offer incentives: Provide time-sensitive discounts or exclusive bonuses to encourage immediate action.

Here’s a flexible structure for just-in-time trigger emails.

Try these subject lines:

  • Urgency/Scarcity – “Don’t Miss Out – Your [Item in Cart/Viewed Item] is Almost Gone” or “[Number] Left! Grab Your [Item in Cart/Viewed Item] Before It’s Gone”.
  • Personalized Recommendation – “Because You Liked [Item/Category], We Think You’ll Love This” or “Complete the Look with [Complementary Item]”.
  • Helpful Reminder – “Still Thinking About It? Your [Item in Cart] is Waiting for You” or “Back in Stock! The [Item You Were Looking For] is Available Again”.

Consider some of these elements for the email body:

Add an immediate attention grabber – Start with a sentence that hooks the recipient’s interest, highlighting the trigger. E.g., “We noticed you added [Item Name] to your cart, and we wanted to ensure you didn’t miss out on our special offer” or “Based on your recent browsing of [Category], we’ve compiled a few recommendations just for you”.

Include product/offer highlight – Briefly remind the recipient what interests them. Include an image of the item or a few related items for visual appeal. If it’s a sale, clearly state the discount and how long it’s valid.

Emphasize value proposition – Emphasize the item’s benefits or the offer’s urgency. Use social proof if applicable (e.g., “This is one of our bestsellers!”). Address any customer concerns (e.g., free shipping, easy returns).

Add clear Call to Action – Make it incredibly easy for the recipient to take the next step. Use a clear and compelling CTA button (e.g., “Shop Now,” “Complete My Order,” “View My Recommendations”). Consider offering a bonus or incentive for acting quickly (if applicable).

Sign-Off: Keep it brief and friendly. Include your brand name and contact information.

Metrics for Monitoring Intelligent Upgrades’ Revenue Impact

It is essential to analyze the following key performance indicators to assess the effectiveness of upgrade campaigns and their impact on revenue generation:

Upgrade Conversion Rate: Measure the percentage of users who successfully upgrade to a higher-tier plan or purchase additional features after receiving targeted upgrade communications. This metric reflects the campaign’s ability to persuade users to invest more in your product or service.

Average Revenue Per User (ARPU): Calculate the average revenue generated per user, including existing and upgraded customers, to evaluate the overall financial impact of upgrade campaigns. An increase in ARPU indicates that upgrades contribute to higher customer revenue.

5. Contextual Win-Back Campaigns: Recovering Lost Customers and Reigniting Revenue

Customer churn is inevitable, but it doesn’t have to be a permanent loss of revenue. Contextual win-back campaigns utilize email to re-engage churned customers, understand their reasons for leaving, and entice them to return.

Understanding Churn Through Data Analysis

Before initiating win-back campaigns, analyze the reasons behind customer churn. Utilize data analysis to identify patterns and pain points, enabling you to create campaigns to address specific concerns and offer solutions that could lead to a renewed subscription.

Targeted Win-Back Email Strategies

Email marketing isn’t just about sending out newsletters; it’s a dynamic engine that can fuel your startup’s revenue growth. From attracting new customers to re-engaging dormant ones, a well-crafted email strategy can significantly impact your bottom line. Winning back lost customers is often more cost-effective than acquiring new ones. By strategically segmenting and personalizing your win-back emails, you can significantly increase the likelihood of re-engagement and revenue recovery.

Segmentation by Reason: Divide churned customers based on why they left. Did they find a competitor’s product more appealing? Were they unhappy with your pricing? Understanding their reasons allows you to tailor your win-back campaign accordingly. For instance, if price was a factor, offer a tempting discount or highlight the value they’ll receive for their investment.

Highlight Improvements: Showcase any updates or new features you’ve implemented that directly address the issues that caused the customer to leave. This demonstrates that you’ve listened to their feedback and are actively working to improve their experience.

Special Offers: Sweeten the deal with irresistible incentives like limited-time discounts, free trials of premium features, or exclusive access to new products. These offers can reignite their interest and make returning to your product or service a no-brainer.

Crafting the Perfect Win-Back Email – Here’s a structured approach for targeted win-back emails, focusing on segmentation and personalization.

Subject Line Options: Grab their attention with a subject line that speaks directly to their reason for leaving or entices them with an offer they can’t refuse

  • Focused on the issue – “We Heard You – [Improvement/Feature] You Asked For” or “[Pain Point Resolved] – See How [Product Name] Has Changed”.
  • Incentive-Driven – “Come Back and Enjoy [Discount/Offer] – Just for You” or “Your Exclusive [Product Name] Discount Awaits”.
  • Personalized – “[Customer Name], We Miss You at [Company Name]” or “Second Chances? We’re Giving You a Third!”.

Consider the following elements for your email body:

Targeted Message Based on Churn Reason – This is where your segmentation comes in. Tailor your message to their specific issue.

  • Pricing: Offer discounts, highlight new pricing plans, or emphasize value.
  • Product Features: Showcase updates that address their previous concerns or introduce new features they find appealing.
  • Customer Service: Apologize for any negative experiences and assure them of improvements.
  • Competitor: Differentiate your product, highlighting unique benefits.

Value Proposition – Clearly explain why coming back is a good idea for the customer. Focus on benefits, not just features. Use testimonials or case studies to reinforce your message.

Special Offer – Clearly state the incentive for returning. Make the offer time-sensitive to create urgency. Provide a clear call to action (e.g., “Use code WELCOMEBACK at checkout”).

Call to Action – Make it simple for them to re-engage. Provide a link to their account or a particular landing page. Offer alternative contact methods (e.g., email, phone) for questions.

Sign-Off – End with a warm and inviting tone. Reiterate your commitment to their satisfaction. Include your brand name and contact information.

Measuring Win-Back Success in Terms of Revenue

To assess the financial success of win-back campaigns, consider the following key performance indicators:

Revenue Generated from Reactivated Customers: Measure the direct revenue attributed to customers who have re-engaged with your product or service after a win-back campaign. This provides a clear picture of the campaign’s immediate financial impact.

Return on Investment (ROI): Calculate the ROI of your win-back campaigns by comparing the revenue generated to the costs incurred in designing and executing the campaigns. This helps determine the overall profitability and efficiency of your win-back efforts.

By monitoring these metrics, businesses can gain valuable insights into their win-back campaigns’ financial effectiveness, identify improvement areas, and optimize strategies for maximizing customer recovery and revenue generation.

Wrapping it up: Email Marketing as a revenue-driving engine for startups

Amplify the efficacy of the above strategies through email automation, streamlining communication, personalizing content, and optimizing the timing of revenue-generating touchpoints. By embracing automation, startups can scale their efforts and reach a wider audience without forfeiting the personal touch crucial for building strong customer relationships and encouraging financial investment in the product or service.

Startups should start early with email marketing, experiment with different approaches, remain adaptable and data-driven, and continuously analyze data to refine revenue-focused strategies. Email marketing is a potent instrument for startups, enabling them to acquire their first paying customers and foster consistent revenue growth.

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