7 Creative prospecting tips for tough economic times

If you can relate to the current climate and are in low spirits because of it, you will appreciate this blog post based on the latest episode of The Modern SaaS Podcast. We had Kris Rudigraap, co-founder and CEO of Sendoso, join us in the show and he shared some really valuable advice on prospecting creatively to stand out in the current economy.

You can watch the full podcast interview on YouTube or listen on any podcast app.

The best way to handle the bleak economic situation at present

The concern around how to navigate the rough waters in sales prospecting right now is a top-of-the-mind question for everyone—including Kris and his team at Sendoso. Kris believes that no one is immune to the sad economic outlook that’s directly affecting so many businesses.

In the recent past—when funding was not an issue—businesses hired as many SDRs as they could and got them to dial phones all day long. Their formula was simple: more reps making calls leads to more pipeline.

And now companies look at it very differently. It’s all about efficiency. In other words, it comes down to retaining the reps who perform the best, and letting go of the rest.

For Kris’ team at Sendoso, the sales team is trying to be more effective and efficient rather than hoping for things to change. That means prospecting is everyone’s job instead of leaving it to just the sales reps. And Kris suggests other companies do the same.

By full-cycle, Kris means AEs who do their own prospecting and generate self-sourced leads as opposed to waiting for SDRs or marketing to hand it to them on a platter.

Things to be mindful about during your outreach

Most sales reps tend to forget that the CEO might own a lot of things in a 30-50 person company, but in a company with hundreds of employees, they rarely are the champion decision-maker when it comes to buying new software.

With more than 500 employees across various functions in Sendoso, Kris is in that boat right now. Kris loves it when a salesperson reaches out to him and refers to one of his colleagues that they might be talking to, rather than asking for his time.

This approach works perfectly well for prospecting to profiles other than CEO too.

Kris is also big on short and sweet cold emails. He likes it even more when a rep sends him a gift or mentions that they are Sendoso customers. That’s a no-brainer—but surprisingly, Kris does get a lot of cold emails from one of his customer companies that aren't personalized or don’t mention Sendoso.

It’s a problem when salespeople don’t leverage the technology available to them to verify the information on a prospect before reaching out to them.

Sometimes we at Avoma get pitched by sales reps for a product we already use. Imagine what kind of impression it sends when you take this kind of an approach with an enterprise-grade company that has multi-year contracts in place with your company.

Modern Prospecting starts with knowing your prospects better

Nobody likes it when someone reaches out to him and asks to “chat for 15 minutes.” People’s immediate thought to this kind of cold outreach is—the salesperson probably doesn’t even know if they are the ideal buyers.

But if they had spent some time researching the prospect, they might have found someone in the company who is a much better fit to start a conversation with.

Also, a low-hanging, situational question like that can be a hit or a miss because, more often than not, the answer to such questions is either a “yes” or a “no.” It doesn’t communicate the value that you are trying to sell.

If you are consultative in your approach—you are helpful and you ask the right set of questions—your ideal buyers will most likely respond to you.

Many times, when you respond truthfully, the sales reps are the first ones to say that they are not a good fit for the prospects. It’s a wholesome experience for both parties because you are glad you chatted and the prospects will think of you if things change for them in the future.

Secondly, with your research, you need to know what’s the preferred medium of communication for someone. For instance, Kris’s voicemail says:

Hey, I don’t check my voicemail. Text me because I prefer to text back.

Despite that, he gets a ton of voicemails. And it clearly shows lack of fundamental research and sheer lazy prosecting.

How you use automation makes all the difference in prospecting

When prospects get cold emails these days, it’s hard for most people to tell the difference between if it’s coming from an automated sales sequence or a real email that someone has personalized for you. And how you use automation can differentiate good prospecting from bad ones.

There is a good reason why there are several multi-billion dollar companies in the sales enablement domain. They have proven to be extremely valuable in improving the productivity of an average sales rep.

However, there’s also the other side of the coin where reps abuse automation to bombard their prospects with a ton of automated emails and ruin their buying experience.

Automated sales tech, when not used mindfully, makes the average salesperson lazy and oblivious to the kind of poor buying experience they might create for their prospects.

Ultimately, you should treat the automated sales tech more like enablers for everyday task management and orchestration. If you do it right, you probably won’t automate them hundred percent through. Instead, you would leave room for yourself to think about the entire prospect journey.

Take the multi-touch prospecting process, for instance. While you can automate some parts of the prospecting process like an automated email nurture, you have to realize that it’s probably one of the many steps that you are going to take to convert them into leads.

You will probably type out a personalized LinkedIn message, call them up on their phones, or perhaps send them a unique gift.

Over the course of your sales outreach, your prospecting should be a mix of automated processes blended with genuine personal touches. It’s more beneficial for the prospects when you are honestly trying to understand their pain points and trying to help them solve their problems.

That’s the risky nuance between using automation for productivity versus overusing it to spray-and-pray your prospects at the cost of efficiency. The point is—if you give an automated tool to an inefficient person, the automation will only magnify their inefficiencies. But if you give it to someone who is a great closer—they will be more productive than ever!

Being intentional with ongoing sales trends

By now, video selling and social selling are table stakes in B2B sales. You can’t talk about them as necessarily modern trends—or be behind your competition in doing it. Thankfully, sales enablement tools are evolving fast to offer better, omnichannel experiences to customers.

Leverage intent data

Intent data has been around in some B2B sales circles for a handful of years. But sales orgs are finally getting better at it. The data is also getting better every year because more and more players are coming into the space.

One of the biggest challenges for B2B sales teams at present is—they have so many different accounts they can sell to, but how can they prioritize them? How can they ensure they are reaching out to the right accounts in their sales outreach? Or, who among those accounts is ready to buy?

Some of these data providers started out originally by offering marketers to use the intent data in their targeting. Over the years, their offerings have trickled into the sales for SDRs to benefit from in their prospecting.

Use AI judiciously

The topic of sales and prospecting in today’s date is incomplete without the mention of artificial intelligence (AI)—another trend that’s taking the B2B sales world by storm lately. Again, it’s not perfect yet and the AI technology is extremely general in its application.

AI solutions like ChatGPT are making a huge difference for sales reps and marketers in crafting conversational and personalized content at scale. But at the same time, the majority of AI-generated content is extremely formal in its tone because its data models the older sales practices when reps used to address prospects as “Dear Sir” or “Dear Kris.”

In reality, sales conversations today are casual in tone and authentic in the way we speak. So while AI does help you generate content at scale and save you time, we have to wait till it gets better at creating authentic content with the right tone.

Where AI does assist sales is in areas that can use automation to bypass human labor—such as in generating meeting notes or summaries or automatically updating them into the right CRM fields. AI does a much better job at researching prospect data and aggregating them into one place, for instance, instead of you manually copy-pasting the data from five different systems.

And that’s also the technique you can apply in areas where AI is not yet perfect. AI brings the research data to your fingertips while you leverage that to create a cohesive messaging by applying your own writing style to it.

For some tasks—like crafting personalized emails—you might still want to have humans in the loop to ensure there are no slip-ups. But if the AI can take the first stab and help you shave off a ton of manual work, that’s still a huge benefit for you to improve your sales performance and shorten the sales cycle.

Get better at ABM orchestration

Account-based marketing (ABM) is another area that has been around in sales and marketing for over five years now, but ABM orchestration is more deeply ingrained in the sales and martech space in the last few years.

The power of ABM orchestration comes alive when salespeople prospecting to new accounts use it to push hyper-personalized ads in targeting their core buyers. It also helps you create the same synergistic messaging hitting a prospect at the same time from all directions. Although to be fair, ABM orchestration is still in its infancy and needs perfecting in the coming years.

A lot of challenges with ABM orchestration aren’t really the issues pertaining to the tools—it’s also the people and process issues that complicate it. Some people are wowed by the idea of ABM while other people and their orgs don’t easily overcome the adoption curve in embracing ABM tools into their processes.

It’s harder for many big corporations who did ABM a few years ago to kick their old habits and adopt new ones just as easily. ABM also requires you to get everyone on the same page like your ads team, field team, SDR team, etc. But it’s easier said than done because the average employee turnover in B2B SaaS is 18 months.

Sometimes, it takes a few years for you to perfect one part of your ABM program. And the next thing you know, a new VP joins your company and now wants to use a different tool or take a slightly different approach to run the ABM program.

This essentially takes you two steps back in your ABM orchestration plan, which is why most organizations (especially enterprises) can’t nail the ABM orchestration or take a longer time to achieve desired results. But there’s a way out.

The way to fix the ABM orchestration problems

Shorter employee tenure and new leadership wanting to bring their own tools is certainly a problem with many companies struggling to see results with their ABM programs.

For early-stage startups that are naive to the idea of implementing an ABM program, it’s just practical to jump in and learn more about running it better with time. For startups that are already running ABM, it’s a Catch-22 situation.

They have several things going on at once and they need to figure out what to focus on in a particular year—and ABM just happens to be one of them. They are brand new and can set up their own processes, but it’s also harder for them to execute because they need to do several things in tandem to be good at it.

One way to solve this problem is to just pick a couple of ideas and run with them. For instance, they can either focus only on running ABM ads or make the marketing and sales teams work together to target the same accounts.

Don’t try to boil the ocean—instead, take one or two ABM initiatives at once, perfect that approach, and then keep building on it.

The kind of ABM campaigns you choose usually depends on several different things, including your company’s growth stage.

The more martech and sales tech continue to consolidate, it’s going to be easier for companies (including enterprises) to connect different tools and manage their ABM campaigns better. Hopefully, a few tightly integrated, all-in-one tools will help everyone easily execute their ABM programs.

Future of SaaS platforms: All-in-one or best-of-breed?

Creative gifting approach to improve your prospecting outcomes

There’s no one-size-fits-all solution in sales prospecting. Some prospects might convert after four phone calls. Others might need a mix of several follow-up phone calls, a chain of LinkedIn messages, and a personalized gift.

Gifting is certainly one of the modern prospecting techniques that helps you stand out from the noise of automated outbound sales sequences. Sendoso offers you one such way for you to build that personal connection with prospects, break through the noise, and make people want to respond to you.

But again, gifting is not a silver bullet that works on every prospect. You still have to think about the buyer’s journey and be methodical about how you approach your prospects.

Gifting as a prospecting strategy looks different for different types of companies depending on their niche, size, and budget—among other things. Some companies will offer you Airpods Pro if you match their ICP and agree to sit for a demo with them. On one hand, this is an exciting prospecting offer—most prospects will be tempted to take it.

Aditya made a LinkedIn post around this last year and the results clearly favored taking the AirPods for free:

But for more serious buyers, this might raise more questions:

Do I really need this product right now?
Should I trade an hour of my time in exchange for Airpods even if I’m not sure about the product?
How will I feel about using some other company’s sales resources if I can’t be helpful to them?

From the seller’s perspective, you have to be thoughtful about offering your prospects a good buying experience even when you have a gifting strategy in place.

Kris recommends that gifting teams incorporate a handwritten note—or a personalized email—that resonates with a prospect along with the gift to make the experience contextual.

It has to be clever, unique, and creative. Using a boilerplate approach like saying ‘hey, I’ll give you Airpods if you give me 15 minutes’ is not a smart move. But if you can tailor that message, it makes it genuinely authentic, creative, and fun.

Not every salesperson can think creatively about gifting in their prospecting process—even when they have the time and other resources to use it. If you think you—or other SDRs in your team—aren’t creative enough about gifting as a prospecting strategy, there are a couple of options.

You can either take the marketing team’s help in running a gifting campaign that includes a good mix of creative content and brand messaging—on top of the gift itself. That way, the sales team can lean on the marketing team’s creative acumen while they just have to be smart around who they opt into the gifting campaign.

A second way is for the sales leaders to help the SDRs or other reps to brainstorm creative ways of gifting on their own. Getting better at creativity is a muscle memory that everyone can develop if they put enough time and thought into it.

If you need inspiration to get started, Sendoso has hundreds of gifting ideas and examples curated under its resource section of the website that you can refer to.

The ROI of gifting is fast and inexpensive

Most businesses perceive gifting as an expensive strategy because it costs money. However, the smartest sales, marketing, and RevOp leaders think about gifting more holistically.

Most revenue leaders invest in a prospecting strategy through the lens of payoff: If I spend $1 in ads, I should get $2 in return. If I’m paying $3 in acquiring one lead, I should get at least $5 in the pipeline. And when you evaluate gifting from that perspective, its return on investment (ROI) is clearly obvious:

When you spend $80 on sending a gift to a prospect, it converts to a meeting four weeks sooner than the traditional channels.

The majority of sales reps spend a month just sending one email after another trying to convert prospects into leads and leads into pipeline. Not only does that undermine a salesperson’s time, it also has zero revenue impact on your sales process.

There’s, of course, some math and science involved in gifting. You always have the choice of choosing between sending a gift worth $20 versus something that costs $80. While a $20 gift is definitely cheaper, an $80 gift usually converts 15 times better. And when you have access to insights like that, gifting becomes a no-brainer business decision.

When you rely on gifting without a bit of tracking or data attribution, it becomes a guessing game that you play with your eyes closed.

Gifting is about creativity, and not the dollar amount spent

It’s a common misconception that gifting is out of reach for small and medium-sized businesses (SMBs) that have a deal size of $20K per year. Kris cautions that small businesses should be a lot more cautious of their spending on gifts otherwise they will end up overspending their gifting budget.

But that doesn’t mean gifting is out of bounds for smaller companies—even during tough economic times. This is where companies have to think creatively about gifting.

You can send your prospects an $8 dog toy because you heard a dog barking in the background while you were doing a discovery with them on Zoom. The impact of that gift is way more than spending $100 on Airpods. Here, the personal touch offsets the dollar amount in terms of the value provided.

Kris cites yet another example where smaller companies have leveraged simple handwritten letters in a $2 envelope with nothing but creative, personalized messages. These might not necessarily be gifts per se, just direct mails that catch the prospects’ attention. But these are definitely high-impact, low-dollar ideas that you can apply to your sales prospecting.

When you look at it from the buyer’s point of view—you are not just making their buying journey easier, but also putting a smile on their face. Sending them a personalized gift shows that you have put in the extra thought and research that goes into it—no matter how small or inexpensive the gift is.

At the end of the day, sales is human to human—and a little bit of thoughtfulness goes a long way. It makes your prospecting stand out in the crowd of automated sales sequences and makes the prospects want to respond to you.

Is gifting effective only for prospecting?

Gifting is not only effective for booking meetings. For stats, only about 20% of Sendoso customers use the gifting platform for top-of-the-funnel prospecting. The majority of the customers use Sendoso throughout the customer journey ranging from:

Improving demo show rate
Onboarding new customers
Sending ‘thank you’ notes
Asking for customer referrals
Celebrating customer milestones
Acknowledging customers’ life events

With Sendoso, Kris has seen some companies sending their prospects a lunch delivery through DoorDash (e.g. pizza) in the morning of a demo call as a reminder. These are effective strategies that drive meeting show rates in the short-term and drive deal acceleration that could have otherwise been four- to six-month sales cycles.

At a higher level, gifting helps you engage and keep the champion entertained in the long term and build your buying committee of 5-10 people—so to speak—that favor you within a customer account that can be helpful to you in the future.

How much of your sales budget should you allocate to gifting?

In today’s economic condition, most companies have cut back their sales and marketing budgets drastically and it’s probably controlled either by the CEO or CFO who doesn’t entertain frivolous campaign ideas.

To leverage gifting in your prospecting process, you first need to convince the decision-makers within your organization and show them its value. You don’t want to be like those companies that spend a lot of time and money doing everything manually.

Instead, you should take a more software-based approach to get where you want to be—especially if you have never specifically leveraged gifting in your sales strategy—and benefit from the consultative advice of the sales team selling gifting products and services.

The problem is—while there are some resources and ROI calculators available out there, the same formula is not going to work for every company. The gifting strategy might vary from one company to another depending on the ACV (annual contract value), the number of accounts that you want to target, your pipeline goals, and several other factors.

It’s best to work backward from these factors rather than trying to find a one-size-fits-all general formula. Buyers nowadays don’t just want more information—they want a sales team who can guide them to the right decision or show them the way to think about something in a certain way.

We would like to leave you with Kris’ parting words:

People buy from people. Get creative. Have fun with it. Get quirky. People know that we are going through some tough times, business-wise. Do whatever you can do to be more creative—that’s the name of the game right now.

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