10 things that quickly grow pipeline every time

No company I have ever worked with has too much pipeline.

“If only we could get to 4x pipe then our sellers would have enough to convert”

During 2000 and 2001 many GTM teams forgot what it meant to generate quality pipeline and now as buyers become stricter with where they spend their money we all need to go back to basics.

You need pipeline now - not in Q1 next year, so here are 10 things you can do today to boost your pipeline.

Note: I was half way through writing this when I realised a number of suggestions also feature on Jason Lemkin’s excellent “10 things that always work in Marketing” which I’m a big fan of. So consider this as inspired by that session.

#1 Pick a niche and learn from your customers

When you have a pipeline problem it is tempting to think about what you can do differently, or how you can increase the volume of activity.

But a lack of pipeline typically means your proposition isn’t landing with customers:

RevOpsCharlie - 5 Whys of Pipeline

The ‘five why’s’ tells us the problem is deeper than an activity or seller issue

So go and speak with them and understand their world better.

This is a job for you as the founder, or at least the revenue leader if you have one.

Pick a niche where you have some customers but think there is a much larger opportunity.

Go and meet with a couple of customers and ask them about their world (not your product).

What are they working on, what is top of mind for them, what are their priorities, what is costing them the most money, where do they see the biggest opportunities to grow. What regulations are they struggling with, which partners are they working with, who is their biggest threat?

If you can, speak with a few different roles in your customer - the CEO, the CFO, the economic buyer for your type of product, the General Counsel, the CIO, the CISO.

Really understand their view of the world just like you did in the early days of your startup.

Take what you learned back into the company and use it to define or refine your value proposition and messaging for this customer segment.

Create content about the problem that your customers are facing specific to their industry and niche.

#2 Bring customers and prospects together over breakfast or dinner

No-one sells better to your prospects than a happy customer.

Having learned from your existing customers about the real challenges they are facing, there is a very high probability that other companies in their space are facing similar concerns.

Most customers are happy to speak at a small private dinner - it puts them on a pedestal, it grows their network, and under Chatham House rules there isn’t an issue around confidentiality.

Organise a small gathering of 5-10 prospects and customers around one of the challenges that your customer raised - “raising capital in 2023”, “managing ESG compliance in a global company”.

To get people in a room the topic needs to be customer-centric, not a veiled attempt to pitch your product - your customer speaker is the hook.

Ask yourself “could my customer get this information from our website?”

If they can, your topic is not good enough - it needs to be content they can only get by being in the room with their peers.

Breakfasts are good because they are the first thing in the agenda so easier to plan for, but you restrict yourself to people that can get there by the start time.

Dinners are good because they are informal, especially after a bottle of wine, but you will see much higher dropoffs as people get tired in the day and just want to get home.

When you were 18 you managed to organise getting 20 people in the same room every Friday - and yet in work we struggle to do it once a year.

Oversubscribe and plan with your restaurant so that whether 7 or 15 arrive it won’t look cramped or empty.

#3 Go and see your customers as the founder

Senior leaders at customers like speaking with senior leaders at their vendors.

They want to learn what their peers are doing at an exec level.

They know that as a founder you also are thinking 36 months out and have insight that can help them understand where the world is headed.

Don’t ask your reps to send a note on your behalf - this smacks of selling.

Instead, if you are going to be in Paris, make the call, send a direct email or text to your peer at the customer,

“Emily, going to be in Paris on 29th-30th Sept, would love to hear how you are getting on with the platform and can share some insights in what I’m hearing from other CIOs on my travels…can also give you a peek into the long range roadmap.”

As a founder you carry some weight, but that meeting has to add value to the customer exec. Roadmaps, insights, connections, visibility, kudos, access - what will she get that she wouldn’t if she didn’t meet with you.

In that meeting, internal referrals are the name of the game. You are looking to expand into new regions, new business units, new functions.

“Who else would you like me to meet while I am here?”

#4 Run weekly webinars

This one is so simple and yet so few do it well.

Have a standing webinar at the same time on the same day every week.

The format is quite loose with perhaps 10-15 minutes of presented content to give some structure and ensure attendees are on the same page, and then 45 minutes of free Q&A for the attendees to raise their own challenges or questions.

You get a lot of benefits with this:

  • Your potential customer is only ever 7 days away from your next event - no more “Why not register for our event in 12 weeks, oh you are away that week…”

  • Prospects and customers get to join a non-threatening event where they can lurk if they want and not have to get MEDDPICC’d by a salesperson.

  • Your sellers have a nice CTA for any call that doesn’t have an immediate next step, “why don’t you join the next Wednesday Webinar?”

Make sure these webinars are not pitches - have a rolling schedule of CSMs, onboarding consultants, solution architects and technical support team members who use the upfront 15 minutes to talk about a specific topic that current customers find useful.

Your prospects get to peek behind the curtain and experience the depth and culture of your team.

You have to be consistent - plan to run 52 of these back to back without a break and regardless of how many people join.

The moment you take a break or say “we only had two people last week, is it worth it?” then you break the cycle and customers can’t rely on being able to drop in.

Record every session and it will create new content for your blog or customer community even if live attendance was low.

#5 Walk the buyer’s journey

A lot has to happen before a customer becomes a true opportunity in your pipeline.

They’ll speak to your partners, they’ll look on product review platforms like G2, they’ll go on industry or role specific Slack communities.

RevOpsCharlie - The Dark Funnel

The Dark Funnel is below the line and where your customer really learns

Have you spent time in that world? Do you know what kind of experience your buyer has in the dark funnel before they get anywhere near your website or an eager SDR?

Go and map out all of the places your buyers hang out. If you sell to CFOs, speak to your CFO about where they look. If you sell to CHROs, speak to your own CHRO.

Don’t just think about your main economic buyer, but consider who they rely on - their CIO, their CFO, their Tech support team - who else is also researching before they put their hands up.

Is the experience in the dark funnel consistent, is it positive, does it encourage potential buyers to get in touch - or do they see your gated content, or the pitchy webinar, or the negative comments by other prospects and decide to keep their identity hidden.

#6 Teach your customers through excellent blog content

You probably have a blog.

Do you read it?

Do you actually learn from it?

Do your customer executives and economic buyers actually learn anything from it?

Or is it just keyword stuffed marketing fluff that an intern wrote with Chat-GPT?

Instead, take the customer insight you learned in #1, and sit down with your most senior roles across CSMs, onboarding, product, support, your own CFO, CISO, CIO, CHRO and you as the founder and have a point of view on these topics.

How would you advise that customer if you were in front of them?

  • Checklists

  • Whiteboard/napkin drawings

  • Diagnostics

  • Project plans

  • Org charts

  • Benchmarks

Ask your onboarding teams what templates or decks they use with real customers when getting them live.

This is the really valuable content that buyers want at the start of their buying process.

Don’t get caught up in a complex content calendar, and asking these people to provide drafts - you haven’t got time.

Get them in a room, with a whiteboard. Film them, just get them to talk to you as if you were the customer. Capture everything and have your content team turn that into the blog post, a recorded video, and infographic, a podcast.

#7 Get on the phone (properly)

The problem with outbound is that you take your most junior and inexperienced team members, give them a phone, email and LinkedIn Navigator and ask them to go and pester your most highly prized prospects.

But your junior SDRs don’t have the depth of experience about the customer’s world - and so SDRs are having fewer and fewer quality conversations per day.

RevOpsCharlie SDR Quality Conversations

Their managers can’t help - they likely came from that SDR role themselves, so whilst they are very good at managing KPIs, they don’t have the true insight around the customer’s problem.

You need to help them - remember the founder-led sales that you used to do? You need to immerse yourself in that again and share your experience with the outbound team.

Take the niche you focused on in step one and schedule time with the outbound team.

Educate them on the customer’s view of the world - the real challenges that they are facing and the opportunities in front of them.

Work with that team to craft some highly personalised messages that you would send if you were reaching out to the executive yourself.

Would you say “noticed you are a retail company?” no you wouldn’t.

But you might say ”was speaking to another of our retail customers who’s struggling with the increased cost of landing product in country….”

If prospects feel they can learn from your outbound team they’ll respond.

Outbound isn’t dead. Bad outbound is.

You can’t expect your junior sellers to know the right messaging without you.

As an aside, remember that your SDRs all grew up in a world where they would never pick up a phone to speak to a friend or family member. They Snap or Whatsapp. Don’t just assume your team have the raw communication skills to speak on the phone - go back to basics and coach them on this - how to behave, how to build rapport, how to listen.

#8 Go to the top customer industry events

Post COVID, in-person events are still popular.

People register much later, there are much higher drop-offs and attendees’ attention spans are much shorter - but industry events provide a unique opportunity to bring prospects in a customer segment together.

But you have to be smart. You can’t just buy the $50k sponsorship and turn up - you need to think from the perspective of the attendee.

Most attendees are there to learn something - so what can you teach them about their own business or industry that they can’t get from anywhere else.

Be creative in how you get your brand in front of them - from their walk from the train station to the event, to their experience of the day, to their trip home - why are they going to remember you over the 250 other exhibitors who are running a raffle for an iPad?

#9 Ask for customer referrals

The highest converting opportunities come from customer referrals - always have and always will.

There is so much noise, so many new products, so many competing priorities, that most people, in their personal life or in business, look to their peers from guidance.

  • “What do you think about the new iPhone?”

  • “Disney+, is it worth it?

  • “Which applicant tracking system are you using?”

But most companies don’t have a formal customer referral programme in place.

Its typically left to the AE or the Account Manager to ask for referrals but as the referral is very unlikely to be in the same territory it never gets asked for.

Make this a strategic programme - “we ask our customers for referrals”, “we get at least one referral per customer per year” and then build this out across marketing, sales and customer success.

For referrals to work best you need to do the work for your customer. Don’t just ask “can you refer us to anyone” but ideally figure out for each customer who you want a referral into - Sales Navigator and 1st party connections are your friend.

Have your closest contact (CSM, AE, AM - even exec sponsor) make the ask,

“Eric, I see you are connected with Aqsa at XYZ, it looks like they are dealing with some of the same challenges that we helped your team with - would you be open to making an introduction?”

They’ll likely say yes, or “Aqsa is not the right person, you should speak with Dennis”

Then provide your contact with a personalised email intro from them to forward on.

  • Make it strategic (don’t just ask your sellers to get referrals)

  • Make it easy.

  • Make it worth it (for both your team and your customer with a little thank-you)

#10 Videos/podcasts with lessons learned from customers

My final suggestion for driving pipeline quickly is customer-focused videos and podcasts.

Most corporate podcasts or videos have a marketing spin on them - a lot of fluff and talk about how great the product is and that now the customer uses the product their company revenues, life and marriage are just so much better.

No one learns anything and listenership/viewership is non-existent.

In the Buyer Experience Audits I do, seeing YouTube videos with just 30 or 40 views is the norm not the exception.

Instead, ask your customer to ‘speak’ to themselves right at the start of their journey.

What do they wish they knew then that they know now.

How was their team structured, what other priorities did they have on at the time, how did they decide this was something they should fix, who was involved, who else did they look at, what advice did they take, what partners did they involve, how did they build their plan, how did they decide their geographical/team roll out, how did they design their project phases, what would they do differently?

This is gold dust for someone at the start of their buying journey and demonstrates to your potential buyers that you know about their world and you understand how to improve their situation.

This kind of content is ideal for your outbound team to use in their messaging or to build into Digital Sales Rooms focused on specific customer niches.

Bonus #11: Speak to your partners

I couldn’t leave this list without mentioning your partners - in a world where buyers are relying even more heavily on trusted existing relationships your partner channel will have an increasing influence on your pipeline.

Partners don’t make it into the main 10 though, because this list is about quickly growing pipeline and you should never think of partners as a quick fix - definitely do not call them up asking “have you got any leads for me?”

That said, if you have an existing partner network of resellers or affiliates, then you can put some quick work in place - you need to take them something rather than asking them for opportunities.

An event/webinar in a box: taking the customer insight you gleaned in #1 can you pull this into a pre-formatted event that you can propose you co-run with your partner. “We’ll bring the content, the speaker and some attendees, you promote out to your wider customer network.” This event could happen in just a few weeks time and impact your pipeline next quarter.

Improved content on the partner’s website: most partner pages on reseller or affiliate websites are generic boilerplate, “ACME is a global leader in talent solutions” - it doesn’t educate or inspire your partner’s customers.

Instead work with the partner team to create useful content for their customers that incorporates your product with their offering. Could you create a calculator or a benchmarking tool? Could they create a healthcheck offering? Help your partner to market to their own customers.

A partner incentive: no-one at your partner wakes up thinking about how they can make your day better. But you can help to keep your products and brand top of mind by launching an innovative partner incentive like these award cards.

The programme could be launched in just a few weeks and you’ll see an initial burst of opportunities that could be in your pipeline next quarter.

Move forward with urgency

These are ten (+1) things you can start work on today.

As companies get larger they get caught up in analysis and planning - only to reach the end of Q4 saying “We were going to start that weekly webinar weren’t we?”

Get someone in charge of all of this.

A Chief Pipeline Officer - call them what you want, but someone that sits across Marketing, Sales and Customer Success and is on the hook for getting your pipeline up to 4x quota.

Let’s go!


Get started

Whenever you are ready, there are three ways that I can help you accelerate your revenue.

  1. Buyer Experience Audit - I’ll impersonate a buyer researching your segment and company and let you know what I find. Ideal for planning your Revenue Operations strategy.

  2. Business Model Design Workshops - I’ll work with you and your team to design or refine a business model for a new or existing product.

  3. RevOps Impact Playbooks - I’ll help you implement one or more tactical processes across your revenue teams - content, referrals, testimonials, adoption and more.

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