This playbook is written for the early-stage B2B startup founder who has experimented or thought about starting their outbound motion.
This playbook is written for the early-stage B2B startup founder who has experimented or thought about starting their outbound motion.
Building a successful outbound motion looks nothing like it did even 4 years ago. Back then, teams would hire 1 or more sales reps to send fairly generic outreach to their entire target market. There was an extremely low barrier to entry. In the end, this basic approach played out very quickly. Prospects smartened up to basic sales tactics. Email platforms got much better at detecting spam material. That brings us to today, where many early-stage startups take off quickly through founder-led, network-based outreach. Things then taper off as teams struggle with the next step of building a successful sales development motion.
The overall process for a successful campaign sounds simple enough:
This guide will break down our step-by-step process for helpling 20+ startups find outbound success through an improved approach to outreach, suited to today’s requirements.
This is one of the first steps most startups get wrong. So many teams put in lots of effort into hiring sales reps, writing copy, and targeting accounts, just for their messaging to land in spam.
Once this goes wrong, it’s very hard to undo. You never want to see your non-sales emails end up being impacted by your mistakes during sales development. Having a high inbox placement rate is the first step for everything else to go right.
This goes beyond just email outreach. Ruining your domain reputation through poor outreach preparation will have other consequences, like reducing the effectiveness of your SEO in the long term.
You have two options here - build your own or send from an existing SMTP server from Gmail, Microsoft Outlook or Zoho.
Building your own mailservers is usually too much trouble for a startup to go through unless they have the expertise. We built our own custom servers to use for our clients for two main reasons:
Using servers from Gmail and Microsoft Outlook are much more popular as it is cheaper and much easier to set up. Each of these servers have their pros and cons. Should you choose this route, ensure you take the following steps first before sending any outreach emails.
As mentioned previously, mistakes made during any part of this process can impact sales outreach, non-sales emails and SEO. The safest step you can take is to send your sales emails from a separate domain that forwards directly to your main domain.
Example: instead of sending from Company.com, you can use:
It’s also helpful to get multiple domains rather than just one. It’s too easy nowadays to get your entire domain in trouble. Just 2 prospects out of 1,000 marking you as spam can hurt your entire domain. That’s why we tell teams to have 1-3 sending accounts per domain. By splitting all your inboxes across multiple domains, you are reducing the risk for just $10 to $30 more.
Another option is using a subdomain - something like sales.company.com. We don’t recommend this unless you really can’t find alternatives to your main domain. Most prospects won’t want to hear from your subdomain - this typically works better for marketing efforts like an email newsletter.
There are three steps to configure. You can skip past these 3 descriptions if you just want to know how to configure them:
To configure these, we've written a guide on follow these instructions for Google and Microsoft. It can take 2 days on Google and 7 days on Microsoft for changes to take effect.
When sending from a new domain, spam filters will treat you as suspect by default at the beginning. There are two ways you can accelerate your timeline to having a a solid domain reputation and getting the green light to begin outbound activity.
Warm up your inbox using an email warmup service for 3 weeks before starting your outreach. There are many reliable options here to choose from, depending on price and capability. Note that as of 2023, Google is shutting down access to their Gmail API to tools that provide a warmup service. This is part of the reason we use our own custom servers for delivery.
Try not to send any outreach during this period. If you must, send 20-30 emails a day during week 3. Then 40-50 per day during week 2. Increase by 10-20 each week until you get to 80/day. This includes your warmup emails. We've covered the step-by-step guide to make the most of email warmup.
Only increase the email volume to 50 emails per day once you are getting a 50% open rate.
Sign up for 10-15 email newsletters. Having incoming emails from reputable domains will boost your domain reputation. This is the list of newsletters we use. Once you sign up, set up filters so that they always end up in your promotions tab.
The most important part of this process is following the guidelines that differentiate cold email vs. spam emails. We've identified the benchmarks you need to be aiming for with your current campaigns.
Spam filters are getting smarter every year. Before you increase your outreach volume, make sure you are following these guidelines:
Here’s how to achieve all of these guidelines.
Bounce rates are all about the quality of your lead list. You have to take extra precaution during a time when people change jobs and email addresses more frequently and data providers like Apollo and ZoomInfo continue to show reliability issues with data quality. If you have a lead list builder, make sure you put the list through an email cleaning tool like Neverbounce or Zerobounce.
There are four ways you can ensure your messages don’t look too similar to a spam filter.
It’s best to be proactive rather than reactive when it comes to spam trouble. Follow the steps above and test your deliverability regularly to ensure everything is running smoothly. We run tests every week for our clients to show their inbox placement rate and how they are delivering to Gmail vs. Microsoft Outlook inboxes. If you wait until your open rates tank, it’s likely too late.
If you do find yourself in this position, start by identifying your issue. If your account is with Google Workspace, begin with Google’s Postmaster Tools. You can also use testing tools like Mail Tester to identify what is causing your issues. They will likely fall under one or more of these reasons:
If your issue is one of the first three, correct them immediately. If you are in spam trouble, here is what to do.
The best defense is to be prepared. Having other domains in warmup or rotation means you never have to compromise on your startup’s outbound volume.
You may also pick up on deliverability issues when you have an account temporarily suspended by Google. This is not a death blow to your outbound, but it is a strong warning sign that you have one or more things that are seriously off at the moment.
10 other steps to get better deliverability than your competition
This is where the best-performing outreach teams distinguish themselves from the rest. The effectiveness and relevance of your outreach is limited by the quality of your research.
This begins by knowing who your ideal customer profile (ICP) is. The best campaigns we’ve run have consistently been for startups that were able to describe their ICP with the most detail.
At the very least, you should be able to map out:
At earlier stages, there may be multiple segments that you want to test. This is a good thing - a big part of outreach is getting answers to your go-to-market questions through rapid testing.
There are a few ways you can pull this information:
Every company starting their outreach has access to these tools and is pulling {{first name}} and {{company}} into their copy. This was considered personalization ten years ago but is tablestakes now.
To stand out, you have to gather research beyond what is easily accessible through a quick glance on LinkedIn. Other ways to conduct research include:
We’ve built a research team to scrape and search for information like this for the clients we work with. The difference in campaign performance is immense for two reasons.
With better research, you are more able to identify who to reach out to within your target market. Information like this breaks down your potential prospects into categories, sorted by who is the best fit for your product. Armed with this information, you can then customize your messaging based on your research to be much more relevant in your messaging.
The other route you can take is personalizing your message to the individual prospect.
Examples include referencing their:
This works when prospects believe you’ve treated them genuinely as an individual, and not just another prospect on your list.
The issue is that most prospects see through this now. There are several AI tools out there that will automate this for you, while reducing the effectiveness of personalization as an outreach method overall for everyone who knows this can be automated.
As a result, the bar for personalization has climbed even higher. This is how you end up with sales reps that will spend an hour writing a single, well-crafted email. The challenge then is scalability. The prospect can read this email and be blown away by your effort, but if they don’t have the need or the timing isn’t right, you’ve burned all your effort. This is why we recommend company and pain-based research over personalization that is either disingenuous (automated) or unscalable.
Once you have your deliverability nailed and have a clean list of prospects to reach out to, conversion will come down to your offer and your copy. We’ve written extensively here on how to write an effective campaign that leads to booked meetings.
There are two parts to the best cold emails - capturing attention, then converting on that attention.
The bare minimum in a campaign to catch your prospect’s attention comes in three parts: your offer, the contact, and the timing. You need to have a great offer, sent to the right person at the right time. If your campaigns aren’t delivering results, it’s because you are falling short on one of these 3 criteria. You can’t control the timing of your prospect’s buying cycle, which is why it’s important to re-engage your prospects every 3-6 months. But you are fully in control of building a great offer for the right person.
Once your prospect has determined that you are worth looking into, there are three things that exceptional emails always contain:
Credibility - Your prospects have to believe that you know what you are talking about and are capable of reliably solving their issues. This is especially true for sophisticated buyers or for products with lots of competition. Credibility can come in the form of social proof, stats, case studies or deep insights into your prospects’ challenges.
Relevance - If your prospects don’t believe your email is targeting a top 3 problem for them, you simply will not get responses. Relevance also means understanding enough about their unique challenges so you can cater your messaging differently to each prospect. An email can become much more relevant through personalization, better targeting, or deeper insights into their pain point.
Engaging - There’s two parts to this. First, is drawing in the reader. This means intriguing subject lines and first lines. The second is writing an email that will leave the reader curious to learn more. If you spell out everything about your features right away, prospects have little incentive to go on to speak to you.
Brevity - Studies show that the most effective cold emails are short in length and digestible to read. This means spacing out your messaging, using simple language, and keeping your writing concise. The average prospect will only give your email a few seconds before they decide whether it’s worth engaging with.
“The winner in a crowded inbox is the seller who can define the prospect’s problem with the most clarity”
It's important to follow up with prospects multiple times instead of just sending one email. A campaign with 3-5 touchpoints allows for adding more value in the follow-up and testing messaging, timing, tone, and ask to improve conversion rates. Threading replies helps provide context, and spacing each email out 3-5 days apart prevents overwhelming prospects. There are also different preferences among individuals within a targeted segment, so it's important to provide a direct pitch or helpful content depending on their preference. As recently as 5 years ago, you could get away with campaigns that sent an email every 1-2 days. It’s better today to space a campaign out over several weeks - this also gives you a better chance of catching them at the right time if timing is the biggest blocker to getting a meeting.
Identifying their preference can be as simple as deeply understanding your target market. A VP of engineering with a sparse LinkedIn profile is likely to prefer short, credible content that they can actually learn from. A demand generation leader might be more open to a more traditional pitch. We use AI tools like Humantic which will break down all of your prospects by their personality type so you can cater your messaging to a style that will appeal with them most.
People generally dislike being sold to. On the other hand, most people enjoy finding solutions to the problems they face and are happy to learn from those who have solved it before. You are selling a conversation at first, not your product. The quickest way to do this is through better targeting. If your research shows that this prospect is a great fit and you can convey that through your messaging, they are likely to read the full email.
Your job is to disarm the objections your prospects will think of as much as possible right away. There are four great ways to do this in a first touchpoint: content, identifying pain points, personalization or a free offer.
Your second and third messages need to add value to the prospect in some way, beyond just “checking in here.” We identified ten tactics you can use for this, as well as more context on the four openers in our Cold Email Guide. There are 14 real-life cold emails at the bottom that led to booked meetings to back this up.
A lot of email-sending features are becoming commoditized with so many tools in the space. The real differentiation comes from your research and sending infrastructure rather than your sending tool. That said, here is our recap of some commonly used tools for sending outbound campaigns.
Free
Streak: Free if you are the only user. This is a decent option if you are sending out just a few messages and doing things completely on your own.
Budget ($60 to $80/month per user):
Mailshake: Intuitive. They carry nearly all of the features of the top-tier tools that you would need apart from ease of use across multiple inboxes/domains.
Lemlist: They offer a unique spin on personalizing images and videos in your outreach.
Apollo: A little more expensive, but provides a database of leads as well. In our experience they had poor for deliverability compared to others.
Instantly: Solid choice if you have multiple domains and inboxes ready to go.
Top Tier (starting at ~$150/month per user):
Salesloft and Outreach. Both are great with marginal differences. Don’t use these until you have two or more sales reps already on your team. They may still require a 3-seat license minimum.
At the early stages, your learnings from outbound testing are just as important as the sales pipeline you build. These are the insights that will feed into customer understanding, future growth strategies and even product decisions. This is all an exercise in achieving product-market-fit.
We tell all our clients that they can't simply A/B test their way into success if their starting point is completely off. But for teams that understand their prospects well and can communicate their messaging effectively, quick iteration can lead to huge breakthroughs.
The volume you want to send will come down to your sales targets.
Sales pipeline from outbound = Outbound volume x conversion to meeting rate
An enterprise motion will require less volume. If you have an annual contract volume below $5K for example, you’ll want to send with higher volume. The modern outbound motion is about being able to optimize for both volume and conversion in a selling environment that is cracking down on both.
We’ve worked with clients that have sent anywhere from 500 to 10,000 prospects each month. You have to run the numbers on your quarterly sales targets, closing rate, and conversion-to-meeting to figure out the sending volume that you need. Then you need to work on the deliverability side of things to ensure that this is achievable without running into spam issues like many startups do.
SDR teams used to test on variables like:
These are all important variables that you need to nail to find success with outbound. A more modern outbound approach, however, tests for variables that aren’t immediately obvious:
This list will look different for each target market.
Most teams run outbound campaigns but still make decisions based on instinct rather than results. We’ve written more here on how to break down your results to understand the direction you should be taking with your messaging on a regular basis.
There have been X big changes to Sales Development over the last 5 years:
The ideal team to build a high-performing sales campaign would have these capabilities:
The issue is that most teams are stuck on a model that was built for an older environment - hiring several sales reps with limited experience to solve a problem of product-market-fit (for early-stage startups). The sales reps that are experienced understand copywriting, but aren’t familiar with how to build an outbound strategy from scratch that is suited to a sales environment that changes every day (I used to be one of them).
The picture is even more stark when you realize that each sales rep will cost $100K (SDR salary, recruiting, benefits, tech) but even more in lost momentum if you hire one and let them go 6 months later like many startups do.
This is why we take a different approach. Rather than throwing more leads at the problem and waiting for magic to happen, we focus on better research and gathering deeper insights. That provides the foundation to gather feedback, iterate and scale outreach, which we can do effectively using custom servers. From there, we can double down on outbound and use these insights as part of a larger go-to-market function (content, ads, website).
Some teams have looked to an SDR agency at the forefront of sales tech. Others have asked their AEs to carry on the outbound load.
This is a comprehensive overview of the basics of finding success through outbound. For more details and tactical steps, have a look at some of the other blog posts we've written.
We help founders and sales leaders solve their entire outbound motion. Zevenue writes your campaigns, manages your sending infrastructure, and handles all your lead list building and troubleshooting to give you differentiated, unique campaigns that lead to real sales pipeline. If you’re working on this right now, let us know what questions you have. Send us a message and we’d be glad to help!
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