Mastering the art of Sales Prospecting, expert edition.
There’s a scene in Glengarry Glenn Ross in which Alec Baldwin’s unnamed character holds out the new leads, the Glengarry leads. Tied together in a neat bow with a red ribbon. He teases the team, and tells them they can’t have them because they cannot close. The symbolism of the magical leads, handed to you with a ribbon is not lost on me.
They are the magical leads we are all after. Too many sales people are waiting for them to fall into their laps. Big news, they are never coming.
The reality for sales people is that they are going to have to do some prospecting. It is a topic that comes up a lot amongst all of the leadership groups of which I am a member and I wanted to get real insight into what modern sales leaders are doing in the market.
This article is for sales leaders and people that want to prospect more effectively, it is based on my experience and my network’s experience and what we think really matters.
A huge thank you to this incredible group of people who volunteered their time, I want to take a moment to acknowledge them and their insights.
Dom Hibberd – Enterprise Sales Director @ Snyk
Dan O’Shaunessey – Sales Enablement coach and trainer @ 29Seven
Mick Gosset – CEO @ Jointflows
Ben Ross – Head of Emea @ Protopie
Marc Parsons – SDR Manager @ One Up Sales
Why does sales prospecting really matter
The data on prospecting can be somewhat contradictory. In the 2024 Ebsta Benchmark survey, they found that outbound was amongst the lowest channels in terms of returns.
In companies over 500 employees inbound leads have the highest win rates and fastest sales cycles, often two times faster. In companies under 500 employees, outbound is the best source, with average deal values typically three times the size of inbound.
However, when engaging the highest performing personas for your offering improved velocity by 488%, indicating that who you engage with matters. This is the behaviour of top performers. The advantage of sales prospecting is making sure you are targeting the right companies and personas to get the best return for your time. Not all leads are equal.
From the sales leaders I spoke to, there were consistenly clear reasons why they felt that sales prospecting was critical. Dom Hibberd said “It is oxygen for reps to breathe”, Dan O’Shaunessy, said “it is the lifeblood, the oxygen of sales to build pipeline”. Ben Ross, echoed the idea of prospecting and building opportunities as being the “lifeblood of the business”. I love these quotes, they were the first things that all of the interviewees said in almost exactly the same form.
They all felt that sales reps need to take their destiny into their own hands. There are just not enough leads to go around to meet your target, and those that exist cannot be relied upon to meet the criteria of target accounts.
My experience has shown me that top performers find their own deals, because they want to have control over their own success and because they can’t do anything else, it is part of what makes them top performers. They are hungry and driven, it just does not occur to them to wait for leads, they make things happen. How do they do this? They follow 3 simple rules.
The 3 simple rules to effective sales prospecting
These seem obvious and intuitive but in all interviews there was almost a maniacal attention placed on them to bring success.
- Target the right prospects – know who is most likely to buy your product or service, don’t waste time on the wrong prospects
- Hone your message – be clear what the persona is trying to fix, how you can help and deliver that message, this is about value not features
- The right mental approach – there are a variety of different approaches but creating the best atmosphere to achieve success was absolutely critical
Target the right prospects
What was apparent from this group was that they had no intention of wasting their time with the wrong targets. The goal for all of the interviewees was to make sure everyone they contacted had a chance of purchasing their product, and that the message they had would land successfully.
This wasn’t just about companies but also personas. Who would hear their message and find the most value in what they had to offer? Without this work you are simply sales prospecting with no real goal. Your goal is revenue not pipeline, the right contact matters.
Ben Ross, used as much automation as possible to build and identify the right targets, creating time and space for the reps to then build their messages. Marc Parsons paid similar attention to this area, focussing on ensuring that the SDRs in his charge had the right target accounts and personas to access in their internal systems.
This is an area where reps can waste a lot of time, make it easy, and keep their attention on where they are most skilled. Focus on the companies that buy your product and the stakeholders who do the buying. The people who feel the pain will want to act fast.
Hone your message
This is about value to the prospect, not your product or its features. Are you clear about their pain points? Are you clear how you can help them? And are you clear how you can articulate that value?
Each persona hears different things so you will need to adjust it, there are layers to the message. How do you get the initial engagement? How do you develop the discussion and how do you get the appointment and all of the stages that follow it?
Mick Gosset felt that this process of delivering the message, as he called it “the elevator pitch” was critical to reps ability to sell the bigger picture and also discovery once the prospect was engaged. It makes a lot of sense, if you cannot deliver your value in a succinct way to engage a prospect, what chance do you have in developing the deal.
CEB insights in their book, The Challenger Sale give some important insights on how you can develop messaging further. They suggest that the best sales prospecting comes down to showing fresh ideas and teaching customers about what’s going on in their world and what problems they’re facing. They give customers new ways of looking at things and share information they haven’t seen before, ultimately they change how customers think.
The best prospectors really know how to land their message. If you want to differentiate yourself, be someone the prospect has to speak to in order to improve their business. Keep it simple in terms of language and keep it to the value you can give the persona.
The right mental approach – different approaches with the same goal
All of the sales leaders wanted to make sure that their reps were in the best possible state of mind to succeed, their approaches varied based on their company culture. It is what they thought about the most and the area where they spent the most time working with their teams.
Marc Parsons’ team are all SDRs so this is a never ending focus for him. He leads from the front making sure he has his leads and appointments on the board, often before anyone arrives into the office. His mantra was “I’m not going to ask you to do something I am not doing.” He felt he should lead through behaviour and this gave him the credibility to drive his team.
Dom Hibberd’s company dedicates one day a week to sales prospecting. It is a fixed part of their culture. I didn’t get the impression it was a missive, more that it was a way of bringing the teams together. Ben’s team worked together with SDRs and Technical Presales to focus on specific prospects, using their combined knowledge of the customers and the market. A collaborative effort that they were all accountable to deliver.
Dan O’Shaunessy, a consultant, was constantly focussing on prospecting. His network approach meant that he was always looking for connections and ways of creating tradable positions to advance both parties in the process. A favour for a favour. What was striking was his ability to be clear where he spent his time, he wasted none of it. He knew where he wanted to get to, and used his direct contacts to do that.
Ben Ross had a different way of keeping his reps sharp. Instead of a day to day approach, he asked them to take on special projects for their sales prospecting. Opening up new ICPs, new markets and new geographies. He felt that by giving his reps an area they could develop for the company it gave them responsibility and drove them to succeed.
I have to admit that Mick Gosset was my favourite. Sales prospecting is their culture. He and his cofounder Hitesh Kapadia are in the fray with their team. When we spoke they were having a prospecting competition across their company, with the results live on LinkedIn. He wanted his team to beat him, he felt that it would give them confidence to push on and succeed. A small team, bonded together in a joint endeavour to build their company. It felt inspiring, even for an old cogger like me.
The outreach plan
All of these elements are the preparation to contacting your target audience. There is no right answer here, only what is relevant for your market, your target personas, your stage and what you are trying to achieve.
Dan O’Shaunessy worked through his network, he has spent years building it and it serves him well. Ben Ross, has a multi channel, very personalised tailored messaging approach. He wants his outreach to be creative and based on introductions that have high conversions.
Mick Gosset, was focussed on outbound telephone contact, as they are a new company with limited awareness. They automated the dialling so there is always another call queued up. High intensity prospecting! Dom Hibberd and Marc Parsons, focussed on calling customers too, their confidence was in the preparation to know their messaging and target audience, backing themselves to engage directly with prospects.
Ultimately someone has to speak to a customer, with email response rates plummeting, it is too easy to sit behind a sequence or a magic email. I am a great believer in multi-channel approaches, but in terms of sales prospecting, keep it sharp, and pick up the phone sooner rather than later. The old method still works very effectively if you can find a phone number!
What to measure
As a CRO, my main goal around demand building is new, qualified opportunities in the sales pipeline. However this big vision approach is not very helpful here, as this is too far down the road. The group were focussed on a much more near term measurement.
The consensus was converted meetings. These leaders wanted to measure something close to the activity so that they could make changes quickly and improve conversions. Is it working? Are we getting meetings? Ultimately they wanted to know that these meetings lead to converted deals, but their focus was on the effectiveness of the prospecting right now.
Any other advice?
There was so much great advice here, to cram it all in I kept it to two categories, those which everyone agreed on and nuggets of insight which I have just to share with you.
What they agreed on
- Do not spray and pray, be focussed
- Offer customers your opinion and be bold
- Don’t pitch or demo, engage on what matters to them
- Don’t go straight to product
Nuggets
- Marc – Be accountable for yourself, don’t take it personally and stop putting it off, you will only regret it tomorrow, so you might as well start now ( I love this )
- Mick – don’t make it a chore, love the interaction, don’t pass up the quality time with your reps in the trenches
- Ben – Personalise and do your research on the contact, take risks with prospects and try different things
- Dan – be ready for the meeting, prepare, let the prospect lead but be their equal, do not be subserviant, build value from the start
- Dom – show you understand their business, this call is about them not just any old call. The more personalised the more effective you will be.
Final Thoughts
I had so much fun writing this article, mainly because this was such an inspiring group of people with which I spoke, and I learned so much from them
The most important learning is that Sales Prospecting is as integral to sales as it always has been. In some ways more important than in the past in such a crowded and automated market flooding prospects with engagement. But get it right and you can close more of the right deals.
Coffee might be for closers, but what all good reps know is that sales prospecting pays the bills.
The NOT so secret CRO 
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