Planning and Managing Outbound Prospecting

Planning and Managing Outbound Prospecting
Jason Bay is the Founder and Chief Prospecting Officer of Blissful Prospecting, a company that provides training and coaching for outbound sales teams. In this guide, he lays out how cold-calling teams can zero in on the right prospects to target, develop repeatable outreach sequences, and consistently generate meetings with a “prospect first, me second” mentality.

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Questions covered in this guide

Why should outbound sales teams invest in improving prospecting?

Salespeople are expensive – efficiency is crucial. Having an outbound function helps you get a better ROI out of your people. 

When should a company invest in formalizing or improving its prospecting processes?

Develop an inbound engine first – having something that really works in that regard is going to prove out the messaging. If the content, case studies, and the messaging really seem to resonate with people and prospects can buy without needing to have someone cold email them or cold call them, that’s going to give you a really good foundation for outbound leads. Now you already have a lot of that messaging in place for the outbound muscle (you can also start your outreach efforts with people who’re engaging actively with your content but haven’t signed up for a demo yet). 

Invest in prospecting systems when you start to scale – where you can run into trouble is if you’re bringing people into a process that hasn’t been figured out yet. As the sales leader and the person that’s going to be hiring, you need to figure out how to make outbound work for your company and vet it out yourself. It’s better to invest in coaching or training just for yourself to figure out your market fit and the tools you need before hiring others. You want to be able to hand an SDR a playbook instead of hiring them and then figuring it out afterward. 

Who’s responsible for designing and implementing prospecting strategies, and who should be involved?

Whoever is managing sales – this person needs to be getting their hands dirty and the one leading the charge. 

The sales leader needs to pick up the phone and cold call – you learn so much by doing this. It’s also really good feedback that you can bring to your product team at the early stages too. You can talk to your product marketing team about what is and isn’t resonating from a messaging standpoint. 

Ops and enablement can help set up the tools and training – once you know that your system works, you can hire for ops and enablement. 

What do you need to define about your targets before you start prospecting?

Replicate your best customers
    1. Figure out what makes a good fit at the account level:
    • Who has been easiest to sell to? Who has the shortest sales cycles and were the people that seemed to “get it?” Look at who has made the best case studies and success stories. Who gets the best results? Think about factors like:
      • Industry
      • Employee count
      • Stage of business
      • Funding
    • Factor in your company’s leadership and investors, who might ideal customer characteristics in mind, along with verticals they want to test out. So you might need to prioritize that as well.
    2. Determine who you need to talk to at the personal level – don’t skip outreach to champions and influencers and only focus on reaching the decision-makers.
    • Identify decision-makers – the people that actually end up signing the deal.
    • Identify champions – everyone always wants to talk to decision-makers, but it’s also important to get to the people who’re going to champion your product, and who can get you the meetings with the decision-makers.
    • Identify influencers – for example, you might want to talk to a sales manager if your software helps with inbound leads, but the marketing department might also be involved in that process. So talking with someone from the marketing department might also help with the decision process.
    3. Identify the values a prospect could have that make your value prop resonate – although a company may look like a good fit for your product based on their numbers, they may not resonate well with what you’re offering. Determine this by looking at:
    • What do they brag about? –  look at their website for testimonials, case studies, and accomplishments. 
    • What do they educate their customers about? – this is important because you could help them do more of this. 
    • What are they spending money on? – tools? Are they hiring? Have they just bought out another company? Are they merging with other companies? Are they opening locations, closing locations?

What are the key activities that go into outreach? 

Outreach – outbound sellers are professional interrupters, be persistent.

Sequencing – plan outreach around the optimal number of activities to get someone’s attention. I use “KISS” (keep it simple sequencing). You’ll have 12-15 activities through multiple channels over 3-4 weeks. You don’t know your prospect’s preferred method of communication, so that’s why you want to spread this out.  

What might a best practice outreach sequence look like? What would the format and content of each touchpoint be?

Sample weekly sequence, 3 weeks in a row: follow this pattern for 3 weeks. Pick one problem you can help with in week 1, focus on a different problem in week 2, and then a different problem in week 3. 

Day 1  triple touch/combo prospecting. Hit them on multiple channels all at the same time. Example: You’re going to leave them a voicemail and say, “Hey X, no need to call me back. I’m about to send you an email.” That cold email says, “hi X. I just left you a voicemail.” And then you’re going to send them a LinkedIn connection request. In your messages, focus on one problem you can help them with.

Day 3 – you’re going to call them, but not leave a voicemail. Then you’re going to “reply all” to your previous email chain, and all you’re going to say is “Any thoughts?” And that’s two more touches right there. 

How do you define good “problems” to focus on?

Don’t pick too generic a challenge – if you do, it won’t be something sticky that they’ll relate to you. For instance, if you’re a company that sells customer support outsourcing, don’t say “oftentimes I hear that customer support teams get overburdened”–that’s a super generic challenge. Instead say, “I was on your website, and I noticed that you don’t have 24-7 chat coverage”.

Personalize with research – you might incorporate a case study; for the customer support example, you might quote a Zendesk study that has shown that most buyers make their decisions between 10 pm and 2 am, so if you don’t have a 24-hour chat service, you could be missing out on sales. 

Look for indicators – for example, when I prospect for my own business, I’m helping people with their cold email and cold call problems, and that’s not something I can research and find they have a problem with directly. So when I’m doing the personalization, I’m looking for indicators that they might have challenges with prospecting. For example, if I see a company is hiring a lot of sales reps, one thing I know is that they want to get them onboarded quickly, and might need help.

What collateral does the team need to produce?

Build a playbook – it doesn’t have to be fancy; it could be a Google document or a Word document. Get everything in one place, then link out to other resources from it and treat it as a table of contents. Include content on:
  • Targeting – spell out the characteristics of an ideal account, what is the ideal client profile, and what are all the parameters around what makes a company a good fit? To illustrate, include links to the LinkedIn profiles of people who are your customers who meet the ideal client profile and the persona. 
  • Sequencing – outline what that sequence strategy looks like. This could be a table as a schedule. You’ll want to have email templates for all of the problems that the prospects might have. You’ll want to have a talk track for the phone call to a prospect, what should the rep say? But allow room for some personalization from reps. 
  • Objection handling – have down what the most common five or six objections are along with, what are the best ways to respond to each one.
Link in a library of resources
  • Content from other top salespeople or people in a niche industry (to help onboarding reps get up to speed on the space.)
  • Articles, posts, and videos that help build prospecting skills, e.g. content on cold calling.
  • Research that could be shared, i.e. if you have your own collateral, or if there’s anything like a third-party case study that validates or educates your reps or their prospects.

What training do you recommend for prospecting?

Have the whole team make calls together – have an hour call block between 8am-11am in your prospect’s local time. Rally people around this. 

Do call and email reviews – once a week, do a team call review. You should have some technology where you can listen to call recordings and where your reps are recording their own calls. Have each rep pick out a call that they would like for you to go over. As a team, you work through and coach so that people can benefit from hearing other people’s stuff – both the positive and the negative. Every other week, do similar cold email reviews. 

If you’re selling something really technical have sellers take classes in that area so they have a decent foundational understanding and understand prospects and what their job responsibilities are. For instance, if you’re selling an online security product, have your SDRs take a course on security.

Role-plays are good, but make them situational and profile-specific – if you have a rep “playing” a CTO, they may not know what that role is really like, so make sure to give them a profile to work with. This will help the rep playing the prospect know who they’re actually meant to be and how they should respond vs. just winging it. 

What are the key skill sets that reps need to drive high conversion?

Empathize → Validate → Offer – usually, people do it backward. For instance, if you get a “not interested” objection, they still do the offer part first, they ask for what they want. Instead, if someone is saying they’re “not interested”, you should:
  • First, empathize with them, think about why they might say that.You might have caught them in the middle of something and they only answered because they thought you were someone else, or maybe they’ve had a lot of bad experiences with cold calls. 
  • Then validate, disarm them with your understanding, say something like “sounds like I totally caught you in the middle of something. If that’s the case, I get why now might not be the best time to talk to you.”
  • Then, you can get to the offer piece, “while I have you, would it be okay, if I just told you real quick why I’m calling, and then you could let me know if you want to keep chatting?”
The same principle applies to other objections – for instance, if they already have another vendor:
  • Empathize with what they’re thinking, probably, “Why the hell would I want to continue talking to you, I already have another vendor?”
  • Validate by reflecting that, “I’m sure you’re probably wondering, ‘why would I want to continue talking to this guy if we’re already taken care of?’ That’s totally fair.”
  • Then go to the next piece and ask for what you want

Use “no-oriented” questions – when making an offer, try a “no-oriented” question, like would it be a bad idea if…? Would it hurt to….? That way, you’re not trapping the person into saying “yes”, because people don’t like saying yes to people that they don’t know. That feels like they’re committing to something, but “no” makes them feel in control. For example “While I have you on the phone, would it hurt if I took 30 seconds to tell you why I’m calling?” 

How should you think about prospecting differently than closing?

Prospecting is not selling – they’re completely different things. One does help the other, but don’t prospect to make a sale, prospect to start a conversation. Make it about the meeting; don’t talk about why you’re better than other people, pricing, or what your features are. During prospecting, educate them about the problem.

“Teach, don’t take” – make them want the educational side. As a prospect, I want to know that I’m not just going to hop on a call and get a demo; I’m actually going to learn something about what other people are doing in my industry.

What tools or resources make good prospecting easier?

A CRM – probably Hubspot or Salesforce.

Database building tool – a tool for finding and saving down leads and contact information, I like Lead IQ.

A prospecting-specific tool with sequencing – e.g. is going to help you run your sequences and make the calls and that sort of stuff. Usually, that tool is separate from the tool you use to find contact information. It’s got data and sequencing in one place, and it syncs up with HubSpot and Salesforce. If you’re further along (a couple of dozen reps and you’re using Salesforce), Outreach or SalesLoft could be a good bet. 

Who’s responsible for building lead databases?

Don’t have your reps do it – even if you’re a startup. Instead, outsource it to virtual assistants or specialist companies. The ones I work with help me pick out the companies and people and help me look for items to personalize the outreach too. Outbound View is a company that’ll build the lists and verify the phone numbers. Upwork can also be a place to find good, inexpensive VA’s. 

How can you incorporate personalization at scale?

Find patterns in a repeatable way – it doesn’t mean that you templatize it and fake the personalization. What it means is that every time I reach out to a company, I know what I’m looking for. Have a checklist of things you could pick out, so you’ll easily be able to have 2-3 things per company. Good things to look for:
  • Accomplishments they brag about
  • What are they spending money on (tools)?
  • Who are they hiring?
  • Have they just bought or merged with other companies?
  • Are they opening or closing locations?
  • What do they educate their audience about?
  • How do they perform on relevant things you can test (e.g. response time)?

What are messaging best practices for prospecting?

REPLY method – “reply” is an acronym (Relevant Results, Empathy, Personalization, Laser-focus, You-oriented), but you work through these in reverse order.
  • You-oriented – it should be about the prospect. If you’re using a lot of “I’s” in the email versus using “you’s”, that’s a pretty good indicator that you’re not focusing enough on them.
  • Laser focus – an overarching idea of being concise. Emails should be under 120 words, three to five sentences. When you talk about what you do in a cold call, it should be 15 or 20 seconds, should be pretty short, and pretty snappy.
  • Personalization – customize the message on emails and other touchpoints.
  • Empathy – people like to know you have problems like theirs, it’s really important to show the prospect that you know a little bit about their world.
  • Relevant results – close with the results you can deliver that are relevant to their job, company, and goals.

Don’t be afraid to be repetitive in messaging – you don’t have to say something different each time you talk to someone. For instance, in the first week of your sequence, you’re going to say largely the same thing in your voicemail, your email, and your call.

The phone is underrated – people think this is dead for some reason, but it’s the best way to get people into a conversation. 

How should AE’s think about prospecting?

AEs should set aside some scheduled prospecting time – the biggest difference is in the schedule. For SDRs, this is a full-time job, where AE’s have more to juggle. But I hardly ever find situations in any company where AE’s have their entire book scheduled out from the SDRs. They usually have to do some of their own prospecting. The best thing to do is to make a rule, e.g. to spend the first hour of Tuesday, Wednesday, and Thursday, prospecting. If AE’s prioritize three to five hours a week, they never run into a situation where they don’t have enough activity going on.

What are the most important pieces to get right?

Grade yourself on the basics: are you identifying the right people, engaging them, and converting them? I always like using fitness as an analogy. If you’re not fit, there are a few things you should be on top of: eating right, being active, getting sleep. Good prospecting is the same, there are lots of things you can do, but ultimately it comes down to getting really good at doing the basics.
  • Identify – do we really know who our ICP’s and personas are? Do we know the language that they speak? If not, interview more customers and talk more about who you’re targeting.
  • Engage – how well are sequences performing? Do people respond to our cold emails? Do we set meetings after our cold calls?
  • Convert – how well are we handling objections?

Make “you first, me second” your keystone habit – really focus on the prospect and what’s in it for them. Yep. Every single interaction, think about what this other person is getting out of it before asking for what you want.

What are the common pitfalls?

Don’t talk too much about your product – people care about how your product helps them. And that’s it. So focus on the prospect and what’s in it for them.

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