From $2K to Fortune 500: How One CEO Perfected Her Cold Email Game in 2 Years

Welcome to Cold Chronicles, our new series where we dissect and analyse some of the most famous and influential cold emails that have graced inboxes. Each week, we’ll bring you a candid, down-to-earth examination of notable cold emails, from startup founders trying to get their big break, to seasoned executives sealing major deals.

We’ll explore how these seemingly simple messages employ language, tone, and timing to weave magic and open doors. So grab your beverage of choice,and get ready to tear apart some fantastic cold emails – where every word counts and the right phrase can turn the tide.

In the first instalment of Cold Chronicles, we’re taking a look at Allie Janoch’s cold emails to attempt to gain funding for Mapistry back in 2015.

Here is the key:

Prospect-centric

Adding value

Offer/ solution / information provided

Pitch

CTA

Pain point

Allie Janoch's 2015 cold email to Jason Lemkin
Allie Janoch’s 2015 cold email to Jason Lemkin

Allie Janoch <allie@mapistry.com>

10/1/15

to jason

Hi Jason,

Thanks for chatting with me for a few minutes yesterday at Berkeley about “uber for enterprise”. The “uber for enterprise” thesis really hit home for me, it’s exactly what we’re doing at Mapistry by replacing environmental consultants and professionals.

We are doing $2K in MRR at the moment, but I would love to talk to you more when we get 10x revenue. I know you don’t typically grab coffee with companies until you are ready to invest, so can I reach out to you in a few months when we are ready to discuss investment?

Thanks,

Allie Janoch

CEO | Mapistry.

We do not have the subject line here, and the salutation “Hi Jason” is a little outmoded in 2024 (when even a salutation is dead space!) but perfectly fine for 2015.

Allie’s ‘cold’ email is absolutely exemplary for one which attempts to gain the attention of a senior with reference to a shared conversation “for a few minutes yesterday at Berkeley”.

Where her email falters slightly is the second sentence, where she claims that the “uber for enterprise” is “exactly what we’re doing at Mapistry”. Although this may be true to some extent, the context of the rest of the email leads us to assume this claim is aspirational, which undermines the authority of the piece. Allie’s framing of “uber for enterprise” not only aims to contextualise Mapistry’s mission but also seeks to make it relatable and memorable for Jason.

Moreover, the transparency of sharing that “we are doing $2K in MRR at the moment”, coupled with the relevant personalisation of “I know you don’t typically grab coffee”, finished off with a clear yet soft CTA, makes this a textbook cold email.

Allie never received a reply! How many perfectly-crafted cold emails suffer the same fate.

Perhaps one issue is the lack of a pain point. Although her email clearly indicates that she understands Jason and his frame, the burning pain of a problem being solved is lacking, which removes urgency from the equation.

Thankfully, we have the privilege of seeing her second attempt to Jason from 2017, which throws the previous attempt into relief.

Allie Janoch's 2017 cold email to Jason Lemkin
Allie Janoch’s 2017 cold email to Jason Lemkin

Date: Thu, Oct 19, 2017 at 5:50 PM

Subiect: Mapistry –SaaS for environmental regulations — Fortune 500 Customers — Seed

Hi Jason,

My name is Allie, and I am the CEO of Mapistry. Mapistry is a SaaS application for environmental regulations at industrial facilities. Environmental regulations are notoriously confusing and complicated, yet the technology used to manage them is usually no more sophisticated than excel spreadsheets and email. This system leaves manufacturing companies vulnerable to multi-million dollar lawsuits and severe damage to their brand.

Traction & numbers:

customers include Fortune 500 companies like 3M, Republic Services, Tesla and Procter & Gamble

growing 15% month over month

September revenue: $67K

fully ramped, our existing customer base corresponds to a $4M run rate.

United States TAM: $3.7B ($1T environmental market globally)

You can check out more details about Mapistry in a short deck here.

I am raising a seed round of funding for Mapistry to maximise on our recent momentum, expand our product to other environmental domains (focused on stormwater to date), and continue to develop software that automates services traditionally provided by environmental consultants.

I’ve been following SaaStr for a while. In particular, I saw your talk with Veeva from the SaaStr conference and I’d love to talk to you about how we fit into this trend of vertical SaaS. One of the reasons so few companies are using software for environmental compliance is that the only tools available are so unspecific and horizontal that the customizations required are so immense, they become unrealistic.

I liked what Peter had to say about services. We also feel very strongly that we have great people and we aren’t going to give their time away for free. We like to think of our environmental services as being paid for sales and/or customer success. In fact, I just did a quick, back of the envelope calculation, and looks like we’ve been doing about 35% profit margins on our services for 2017, which has been a nice source of revenue for the rest of the company while we get off the ground.

I’d love to schedule a time for a 30-minute phone call or coffee. Do you have any time the week after next?

Allie Janoch

CEO | Mapistry

First and foremost, the subject line is stellar – at once descriptive, visually compelling, and curiosity-inducing, it is the perfect way to initiate an email.

Moreover, whilst Allie’s previous attempt had started by referencing their brief conversation, her 2017 email frames her as a CEO, and introduces Mapistry off the bat. Whilst this may come off as salesy, the incredibly specific pain point that follows it indicates that this isn’t a generic pitch, and allows for the indulgence of opening the email referring to oneself, which can be considered bad practice in the present day.

Leading with the pain is best practice, as it foregrounds the reason for Allie’s business and in turn, the reason for the email.

Next, by providing specific financial figures, customer names, and market potential (TAM of $3.7B), Allie crafts a compelling narrative that demonstrates the company’s traction and future potential. Moreover, by using jargon and industry-specific terminology, Allie positions her and Jason within the in-group to signal status and belonging.

The presentation of a small deck with a link for each of access is exemplary, indicating respect for Jason’s time, whilst not labouring the deliverability of the email by attaching it directly, which could lead to it being directed to spam.

Furthermore, her mention of a recent funding round this time is combined with the reasons for the round, (“maximising momentum”, “expanding product,” and “continuing to develop software.”) and this added specificity builds towards the CTA, adding context for the email without being explicit.

This line of reasoning comes to a head when Allie mentions Jason’s talk, and connects the dots that they could collaborate on the SaaS vertical, before providing another pain point! Although not strictly necessary, Allie is indicating that the collaboration has been well-thought out.

By mentioning insights from industry leaders like Peter and highlighting their 35% profit margin for 2017, Allie demonstrates that Mapistry is knowledgeable and profitable. Explaining how these profits help sustain the business highlights smart financial management and long-term planning, making a strong case for investment and immediate engagement.

Finally, unlike the reserved proposition in the 2015 email, Allie now concludes with a strong, specific call to action, suggesting a 30-minute phone call or coffee meeting with two potential times. This not only prompts immediate engagement but also simplifies decision-making for Jason – whereas the 2015 email follows best-practice with a soft CTA, this email has provided such a fulsome narrative and so much context that the strong CTA is justified.

Are there some things that could be different? Sure.

  1. Leading with so much personal context may only work with seniority – otherwise, being prospect-centred is preferable
  2. Two pain points and two CTAs is one too many
  3. It could be a little shorter

Would you have considered this email worth responding to?

Jason certainly did! The very next year he led Mapistry’s seed funding round of $2.5m.

Super Benji enables businesses to efficiently tailor their communications to each individual recipient, enhancing engagement and conversion rates through highly targeted, relevant content. If you want this kind of impact but don’t have the time to personalise every email, try the demo to have your network activated in no time.

AN Introduction to Triggered Lead Nurturing

Behaviour-triggered lead nurturing has emerged as a powerful strategy – it is based on the idea of sending them down the funnel in a way that is tailored to their needs, based on how they behave on-site – which pages they visit, what content they look at or search for. It’s a method that has transformed how companies guide prospects through the sales funnel.

In this first article on triggers, I’ll present the statistical effects of triggered campaigns.

Forrester Research found that companies excelling at lead nurturing generate 50% more sales-ready leads at a 33% lower cost per lead. This isn’t just a marginal improvement; it’s a significant shift in both efficiency and effectiveness.

These companies see a dramatic reduction in ignored marketing-generated leads, from 80% to 25%. This improved alignment between marketing and sales is crucial for overall business success. Moreover, there’s a 7% increase in win rates on marketing-generated leads and a 6% decrease in “no decisions.”The effects are paralleled in sales performance, with companies adopting this approach report 9% more sales representatives making quota and a 10% decrease in ramp-up time for new reps.

Moreover, Nucleus Research found that marketing automation drives a 14.5% increase in sales productivity and a 12.2% reduction in marketing overhead. This allows sales teams to focus on high-value activities requiring a personal touch.

Aberdeen Group reports that companies using marketing automation experience 53% higher conversion rates from marketing response to marketing qualified lead compared to non-users. This efficiency often translates to shorter sales cycles.

Epsilon research shows that 80% of consumers are more likely to make a purchase when brands offer personalised experiences.

MarketingSherpa revealed that 73% of B2B leads are not sales-ready when first generated. Behaviour-triggered nurturing can help reactivate these leads, turning potential losses into valuable prospects.

The Annuitas Group found that nurtured leads make 47% larger purchases than non-nurtured leads, highlighting the value of strategic lead nurturing.

Audience Understanding:

Develop detailed buyer personas. ITSMA found that while 44% of B2B marketers use buyer personas, only 15% use them effectively.

Customer Journey Mapping:

Salesforce research shows that 80% of customers say the experience a company provides is as important as its products and services.

Trigger Identification:

HubSpot reports that trigger-based marketing emails can generate 624% higher conversion responses compared to batch and blast emails.

Content Development:

Content Marketing Institute found that 72% of marketers say content marketing increases engagement and leads.

Marketing Automation:

According to Adestra, 68% of businesses use automation in some way.

Continuous Analysis:

Forrester Research states that 89% of digital businesses are investing in personalisation, including AI and machine learning for analytics.

In my experience, the key to successful behaviour-triggered lead nurturing lies in the balance between automation and personalisation. While automation provides the scale, it’s the personal touch that closes deals. I’ve seen campaigns fail because they relied too heavily on automation without considering the human element, whereas personalisation without a scaling solution can be incredibly laborious. By leveraging data and automation to deliver personalised, timely communications, businesses can dramatically improve their lead nurturing effectiveness. The statistics support this approach compellingly, from increased ROI and sales productivity to higher conversion rates and larger purchases.

In the next article, we’ll explore the types of triggered campaigns and best practices for implementation, before concluding the mini series by identifying the Key Triggers and KPIs for B2B Lead Nurturing to achieve. greater precision in marketing and sales.

If you don’t know where to start with triggers, or have a good idea of how to use them but no means to implement, try Super Benji to keep a virtual eye out on all of your prospects starting today.

The Future of B2B Email Marketing

As we navigate the complex and ever-changing landscape of B2B marketing, it’s more important than ever to stay ahead of the curve and anticipate the trends that will shape the future. This not only ensures that your marketing strategies remain relevant and effective, but also provides a competitive edge in a saturated market. Here are the top 10 trends that are set to redefine the future of B2B email marketing in 2024.

1. Address Privacy Concerns

In today’s digital age, where data breaches and privacy violations are becoming increasingly common, privacy has emerged as a major concern for both businesses and consumers. A comprehensive study by Cisco revealed that a staggering 84% of consumers want more control over how their personal information is used. Being transparent about how you use data and implementing robust security measures can help build trust with your audience and foster long-term relationships.

2. Segment Audience Lists

While segmentation is not a new concept in email marketing, its importance in the current marketing landscape cannot be overstated. According to DMA, 25% of revenue share comes from a segmented list of emails, and sending targeted emails to these segments brings 30% of revenue. Moreover, segmented campaigns had 14.31% higher open rates and saw 101% more clicks than non-segmented campaigns. By segmenting your audience based on factors such as industry, job role, and engagement level, you can deliver more personalised and relevant content, enhancing the effectiveness of your email marketing efforts.

3. Email New Subscribers Within 24 Hours

In today’s fast-paced digital world, timing is everything. A study by Experian found that welcome emails sent within 24 hours of subscription have a 58.7% open rate, indicating audiences value speed and efficiency in sales cycles. By reaching out to new subscribers promptly, you can capitalise on their initial interest, start building a relationship right away, and set the stage for future interactions.

4. Leverage Generative & Analytical AI

Artificial Intelligence (AI) is revolutionising the world of B2B marketing. Generative AI can create personalised email content that resonates with your audience, while analytical AI can predict customer behaviour and optimise email timing for maximum impact. The adoption of AI in B2B marketing is expected to increase by 270% over the next two years. 80% of B2B marketing executives believe AI will revolutionise their industry by 2025. Leveraging AI for your email marketing strategy this year before its widespread integration could provide a significant competitive advantage.

5. Embrace Interactive Email Experiences

Interactive emails, featuring elements like quizzes, surveys, and videos, can significantly boost engagement and conversion rates. According to Martech Advisor, Interactive subject lines have 70% higher conversion rates. By offering an engaging, interactive experience, you can stand out in crowded inboxes and create memorable interactions with your audience.

6. Incorporate Visual Trends in Email Design

Visuals are a powerful tool in email marketing. Incorporating the latest design trends, such as 3D graphics and animation, can make your emails more appealing and memorable. A study by Venngage found that 21.9% of marketers reported that over 75% of their content this year was all about visuals. Additionally, 34.3% disclosed that visual content made up at least 20-50% of their overall content marketing strategy. By staying abreast of visual trends and incorporating them into your emails, you can enhance the visual appeal of your emails and improve engagement.

7. Optimise for Mobile

Over 61.9% of emails are opened on mobile devices, accounting for roughly 1.7bn users daily, and therefore mobile optimization is no longer optional—it’s a necessity. Emails that aren’t mobile-friendly can lead to a poor user experience and lower engagement rates. By optimising your emails for mobile, you can ensure a seamless experience for your audience and improve the effectiveness of your email marketing efforts.

8. B2B Marketing Podcasts Get a New Life

Podcasts have seen a resurgence in popularity, and B2B marketers are taking note. Including podcast content in your emails can provide value to your audience, position your brand as a thought leader, and create a deeper connection with your audience. In general B2B audiences are highly engaged with podcasts, with 51% of respondents across a range of job titles (including owners, founders, executives and employees) listening daily. An additional 24% also reported listening between 2-5 times a week on average. As podcasts continue to gain traction, they offer a unique opportunity for B2B marketers to engage their audience in a meaningful way.

9. TikTok Matures into a B2B Marketing Channel

While TikTok has traditionally been associated with B2C marketing, more and more B2B marketers are leveraging the platform’s staggering 1.92 billion users as of 2023, a 16% increase from the previous year. Tik Tok users are younger and therefore more impulsive, so whilst the average TikTok ad conversion rate currently sits at roughly 1.1%, some 55% of TikTok users have made an impulse purchase on the platform. Within B2B marketers, 61% of respondents said their company has a TikTok channel. The other 39% of people claimed the main reason their business doesn’t use the platform is that the app’s demographics don’t align with their target audiences. As TikTok continues to mature as a marketing channel, it offers exciting opportunities for B2B marketers to connect with their audience in new and innovative ways.

10. A/B Test Subject Lines

Subject lines can make or break your email campaign. A/B testing different subject lines can help you understand what resonates with your audience and optimise your open rates. According to Campaign Monitor, A/B testing can increase conversion rates by up to 49%. Only about 61% of marketers use A/B testing to improve their marketing performance, so the opportunity is there to beat out your competition.

As we look to the future of B2B email marketing, these trends offer exciting opportunities to connect with your audience in new and meaningful ways. By staying ahead of the curve and proactively implementing these trends, you can ensure that your email marketing strategy remains relevant, effective, and impactful.

Now, let’s talk about a tool that can help you implement these trends effortlessly – Benji. Benji is more than just an AI tool; he’s your best sales friend. He’s playful yet hard-working, and he’s committed to automating the sales process in a way that’s both effective and enjoyable. He identifies triggers in the lives of your prospects and crafts personalized emails that are relevant, timely, and fun. He’s not just a tool; he’s a part of your team, trained by you to be the best version of you.

Benji believes in the power of personalization and the importance of value in every message. He can accomplish data enrichment, email and LinkedIn outreach, and deliverability, all while avoiding spammy spray & pray tactics. He patiently follows all of your contacts, sniffing out personal updates that trigger him to draft an ultra-personalized and impactful message that matches your tone of voice.

So, why not give Benji a try? Book a call and see what this hard-working, fun-loving AI tool can do for you. After all, no one should have to work like a dog, except for Benji. He’s ready and eager to help you take your email marketing strategy to the next level.

10 Tips To Improve Lead Quality

In the vast and often unpredictable sea of lead generation, quality trumps quantity. The salesperson is like a seasoned fisherman sorting through his catch, pawing through nets of fish to find the prime catch. At a certain point, the fisherman hasn’t the time to sort through hundreds of catches every day, and has the luxury of being selective about the type of fish he wants to catch.

I’ve heard it said that “It’s easier to sell one really expensive thing to one really rich person than many cheap things to many poor people.” This is the predicament of the successful B2B salesperson – with a sea of prospects, they need only cast to the ICP.

So without further ado, here are ten tips to refine your lead generation strategy and ensure you’re attracting your ideal prospect.

1. Update Buyer Personas

Understanding your audience is the cornerstone of effective lead generation, so regularly updating your buyer personas ensures your marketing efforts are segmented and efficient. Segmented campaigns drive 30% more email opens and 50% more click-throughs than non-segmented campaigns.

63% of content marketers already actively create persona-centric content, and customer centric companies are 60% more profitable than those that are not customer centric! More than 60% of companies that have updated their buyer personas within the last six months have exceeded their lead and revenue goals, so consistently updating the persona will allow you to be profitable long-term.

Three to four buyer personas account for over 90% of a company’s sales. Using more buyer personas also allows for further segmentation, and according to a recent study, companies that segment their leads can increase their conversion rates up to 355%, leading to increased revenues up to 781%!

2. Define Brand Positioning & Apply Consistently

Clear and consistent brand positioning makes your business stand out in a crowded market. Brand presentation consistent across all platforms can increase revenue by up to 23%, and it goes hand-in-hand with trust in brands, with 81% of consumers stating the importance of trust before they spend with a brand.

Consistent branding also serves to clarify what your brand stands for and attract leads that resonate with your core values and offerings – with 53% of consumers saying they need their brands to take a stand on at least one social issue, brands are huge entities that can take a hit if they’re seen to be on the wrong side of moral questions.

3. Implement a Full-Journey Strategy

A holistic approach to the customer journey attempts to ensure no potential lead falls through the cracks.

From awareness through to decision-making, tailor your customer experience journey and content to improve lead quality and enhance the overall customer experience. Given that 94% of buyers reported using online research at some point in the purchasing process and are now more averse to talking to reps, it’s important buyers can make a decision by themselves.

4 in 10 B2B companies believe they’ll have a full vision of their customers in the next few years. Given that 77% of B2B customers said their last purchase was complex or difficult, it’s possible many B2B agencies suffer from survivorship bias which might obscure the reality of how they’re generating quality leads.

4. Adapt Your Landing Page

Your landing page is often the first impression prospects have of your brand. Given that the average landing page conversion rate across all industries is 2.35%, you must make it count by ensuring it’s optimised to meet the expectations and needs of your target audience. Interestingly, long landing pages can generate up to 220% more leads.

Regular A/B testing and updates to the design, content, and call-to-action can significantly increase conversion rates.

5. Ask Detailed Questions

The quality of leads can be significantly enhanced by asking more detailed and slightly invasive questions. 30.7% of marketers say the ideal number of questions on a landing page form to get the best conversions is four, whilst another study of e-commerce brands found that the highest number of converting form fields is 3, with an average conversion rate of 10%.

There’s no one-size-fits-all, and if you want better quality leads, you might use a higher intent form type to provide a review screen, operating as an “Are you sure?“ for the user before they submit. This might include queries about budget, project timelines, or specific needs. Prospects willing to provide this information are generally more engaged and have a genuine interest in your offerings.

6. Tidy Your Funnel & Clean Your Lists

Streamlining your sales funnel removes unnecessary steps and makes it easier for high-quality leads to connect with your brand, whilst tidying up your data allows for proper utilisation of leads that may have got lost. With 51% of companies using marketing automation tactics, a considerable amount of dirty data is being collected, which IBM estimates that bad data costs the US economy about $3.1 trillion per year!

A funnel may have more than normal churn if you have bad onboarding or no ongoing customer success, product problems, poor retargeting, or a score of other factors. Your data might have been sullied by improper formatting, duplicate data, or outdated leads.

Keep your data clean and your funnel efficient to minimise churn and maximise outreach.

7. Provide Valuable Lead Magnets

Offering something of value in exchange for contact details is a tried and tested method to attract quality leads. The average conversion rate for lead magnets varies from roughly 5.2% to 24.2%. In a small study of SaaS companies, the best converting lead magnet type was written at 27.6% and visual at 20.7%, with video and monetary value tied at 17.2%. Whether it’s a free ebook, a webinar, or an exclusive trial, make sure your lead magnets are irresistible and relevant to your target audience, and specific enough that it attracts only your ideal persona.

8. Create Hyper-Targeted Content

Content that speaks directly to the needs and interests of your target audience is more likely to attract qualified leads.

63% of marketers create content by their buyer personas, and persona-based content increases customer engagement by six times when cold leads are targeted! Use insights from your updated buyer personas to create content that addresses specific concerns, questions, or needs relevant to your audience segments.

9. Ask for Referrals

Leveraging your existing customer base to gain referrals is a powerful way to generate high-quality leads. B2B companies with referrals report a 69% faster close time on sales. B2B organisations with referrals encounter a 71% higher conversion rate. According to B2B marketers, the average conversion rate for referrals is 11%. Referrals produce the highest lead-to-sale conversion rates.

Satisfied customers are likely to refer others who are also a good fit for your business. Encourage this process through incentives or simply by reminding customers of the value they’ve gained from your offerings. This also ties into social proof which is a powerful marketing tool – research indicates that landing pages using testimonials experience a 34% increase in conversion rates.

10. Increase your price

If you have too many leads, your supply should meet the elevated demand by increasing the price. Isn’t the free market wonderful?

Improving lead quality is an ongoing process that requires attention to detail and a deep understanding of your target market. By refining buyer personas, enhancing brand consistency, and engaging prospects throughout their journey, businesses can significantly improve the efficiency of their lead generation efforts.

No matter what, when you focus on lead quality over lead quantity, you are almost certainly going to generate a lower overall number of leads. Many of the strategies mentioned above are purposefully designed to ward off low-quality users who aren’t ready to speak to anyone. That means volume has decreased, but the percentage of the good quality to bad quality leads should be moving in the right direction. Before you embark on any of these optimizations, you should discuss the potential outcomes with your marketing, leadership, and sales teams to ensure that everybody is on the same page and no one is caught by surprise with a decreased lead count.

Transitioning into practical solutions, let’s talk about Benji, an innovative SaaS product that epitomises the philosophy of smart, efficient, and personalised lead generation. Benji is not just a tool; it’s a game-changer in the B2B sales landscape, designed to automate and personalise email outreach and lead nurturing.

With the capability to scrape trillions of data sources and identify real-world triggers, Benji ensures that your outreach is timely and relevant, significantly increasing the chances of building trust and rapport with prospects. It eliminates the often overwhelming stress of managing numerous prospects, crafting the perfect subject line, and pinpointing the optimal moment for engagement.

Imagine a tool that does the heavy lifting for you, allowing your sales team to focus on what they do best—selling. Benji is that partner in the sales process, tirelessly working to ensure every prospect is reached with the right message at the right time. In a world where personalised communication is key, Benji stands out as a beacon of innovation, making it an indispensable asset for any sales team aiming to not just reach but engage and convert their target audience effectively.

In conclusion, if you’re looking to revolutionise your lead generation and nurturing process, giving your sales team the ultimate edge, it’s time to consider Benji. It’s not just about automation; it’s about smart automation that aligns perfectly with your sales strategy, ensuring maximum efficiency and effectiveness.