Build a Winning Sales Playbook


Dani Buckley is the General Manager of LeadG2, an 100% remote inbound marketing and sales enablement agency, which focuses on sales results for B2B and B2C companies that have complex, multi-channel sales processes. 

LeadG2 started in 2011 as sales consulting firm that needed to generate leads for its business. Its first clients were media companies that owned television and radio stations . . . and needed to get advertisers.

In the past, B2B sales professionals have tended to have a lone wolf mentality . . . sales didn’t “count” unless the salesperson independently discovered and chased down a lead. Dani feels it is important to change that culture, to supplement cold calling and outbound prospecting with inbound and lead gen.

Dani defines sales enablement as “whatever you need to do to help your salespeople sell smarter and faster.” She spoke at Hubspot Inbound 2019 on “How to Build a Sales Play in 30 Minutes or Less.” In this Marketing Agency Leadership Podcast, she provides a brief overview of the process of developing a sales play:

  1. Develop a strategy by extracting the best knowledge and information from your leadership and your salespeople and from industry best practices and sales best practices 
  2. Create a simplified process that outlines the five things salespeople need to do to identify quality prospects
  3. Identify the technologies and tools salespeople need
  4. Determine the content and resources salespeople need
  5. Plan the rollout
  6. Provide training

LeadG2 builds robust customized “thick stack” sales playbooks for its clients, using PowerPoint so that sales managers can easily update the material. LeadG2 recommends that companies store their most up-to-date sales playbook versions where they are easily accessible by the sales team – where they would normally put stuff in the cloud.

Dani also references Donald Miller’s StoryBrand and the “hero’s journey. She emphasizes that, in messaging and in content development, you/your company is not the hero . . . your customer is the hero. 

LeadG2’s parent, the Center for Sales Strategy, is a 36-year-old sales consulting and sales leadership training company. A brand-new sister company, Up Your Culture, focuses on helping companies improve company culture and employee engagement.

LeadG2 is on Twitter and Facebook. The company website is: Dani is on Twitter @daniobuckley and LinkedIn.

ROB: Welcome to the Marketing Agency Leadership Podcast. I’m your host, Rob Kischuk, and I am joined live and in person by Dani Buckley. Dani is the General Manager of LeadG2. She’s based in Seattle, but the company is 100% remote, which is pretty cool. Let’s dig into some of that. Welcome to the podcast, Dani.

DANI: Thanks. Glad to be here.

ROB: Yeah. Dani, why don’t you start off by telling us about LeadG2 and what makes LeadG2 great?

DANI: Sure. LeadG2 is about 8-9 years old now. We’re an inbound marketing and sales enablement agency. We really focus on sales results. That’s what makes us unique, because our parent company is a 36-year-old sales consulting and sales leadership training company called the Center for Sales Strategy.

We’ve been a HubSpot partner since Day 1, 2011, and work with a lot of other platforms as well. But proud HubSpot partner. Been doing this and helping all kinds of businesses, but definitely specialize a bit with B2B.

ROB: I was going to say, what’s a typical client? It’s a B2B anything? A software company? And where are they at in their own journey as a company when they’re meeting up with you?

DANI: Because of our parent company, we started out working with a lot of media companies – think organizations that own TV stations or radio stations around the country. That was where we started with the B2B side of that, helping them get more advertisers.

ROB: So, they’re calling car dealerships to get combination billboard/radio/TV ads, newspaper.

DANI: Exactly. In the media space, most weren’t doing any marketing. It was 100% outbound sales. So that’s where we started, because our roots from our parent company specialize in media. But it’s really expanded much further beyond that in the last 8 years.

We work with B2C and B2B. It’s all across the board. We’ve worked with industrial boiler companies to home improvement companies to financial investment firms. It’s very broad. Staffing and PEO companies, a lot of that. But it tends to be organizations with a complex sales process. They maybe have multi channels that they sell through, they might have B2C and B2B. That tends to be our sweet spot.

ROB: The media market seems like an interesting place to have started, because on the one hand they are always looking for more ways to bring money in the door, but they are also, I think a lot of the salespeople, probably coming from a very transactional mindset. How do you take an organization like that and help them understand a customer journey and something that happens before a sale? What are you feeding into the pipeline in that media scenario?

DANI: Typically, good media salespeople do understand the buyer’s journey, because oftentimes they’re actually talking about that to their advertisers. So, they do have a good understanding of marketing; it’s just that it’s not actually being employed at their company to do that. So, there is a learning curve.

It tends to be really getting them to understand and trust that lead gen can help them. There’s often this lone wolf mentality in a lot of B2B sales, actually, that focus on outbound and prospecting and cold calling of like, “It doesn’t count as new business or me getting the job if I didn’t find that lead on my own.” Getting that culture shift actually is something we’ve found to be really important with a lot of companies shifting to – you can supplement cold calling, outbound prospecting with inbound and lead gen, and it really works together. We’re not about replacing it. We believe in both.

ROB: Right. You have been with LeadG2 very close to the inception of the company. What is the origin story of this company and your own rise in leadership while you’ve been there?

DANI: I was the second employee hired and became the general manager about 3 years ago. Our managing partner, who founded LeadG2, he was ready to have someone else take over – in his words, “take things to the next level.” His name is Matt Sunshine, and really, this was his idea that came about. It started with the Center for Sales Strategy, our parent company, him looking for ways to diversify our own new business development.

He started researching probably 9 years ago, figuring out: What can we do? Do we buy lists? What do we need to do? Of course, at that time, in its infancy, inbound marketing and content marketing came across and he was like, “Yes, this is it.” So, he did it on his own, started a blog. It was really successful for a year. To this day, inbound marketing is our number one source for new business across the company. Then he said, “Wow, we need to help our customers with this.” So that was the birth of LeadG2, essentially.

ROB: That’s very fitting that the agency actually started eating its own dog food. It started actually doing the thing that it purports to do for other people, and that’s a struggle I think for a lot of agencies and groups like that, to actually do the marketing, do the branding, do the website development for themselves.

DANI: Yeah, I couldn’t agree more. I think that actually makes us a little unique because we didn’t start out as an ad agency or a website development company – which is great. Many inbound agencies have that experience. We started as a sales consulting firm that needed to generate leads, and we were able to do it well.

ROB: You mentioned sales enablement. That word can be a big word; it can be a confusing word. Some people don’t know what it means. What does sales enablement mean right now in 2019?

DANI: For us, it’s whatever you need to do to help your salespeople sell smarter and faster. That’s the way I like to position it. We put it into a couple categories of strategy, the strategy and the processes, which involve things like sales plays and your sales process, as well as the technology and tools that are going to enable them. Then the third tier, we look at content. What are the content and resources they need? The last thing is the training. We have those four tiers.

ROB: I can see where each of those different things that you solve would be a complete stop, stuck in the mud for a company. They don’t know the process, or they bought something and they’re not using 5% of it.

DANI: Yeah. I think what often happens is exactly what you just said. Someone might say, “This is what we need,” so they get the technology and they have all these tools, but they don’t actually have the strategy to back it up or the content to drive it. You kind of need it all. In my opinion, at least.

ROB: There’s a certain irony, I think, that sales software is very widely adopted and kind of hard to use. It’s used by a lot of companies that want their own product to be easier to use than the sales software that they are using. Why do you think sales software ends up so complex that it needs almost its own system administrator type of role?

DANI: That’s a good question. There’s a couple of reasons, I would say. One is that I think – oftentimes when we think of sales software, we think of a CRM – it’s created with the leadership in mind. It’s the millions of things that a manager would want to be able to micromanage, to see activity, to report, to forecast. All things that are very important, but it’s like, what are all the things that they could possibly want? Because that’s who you’re selling to.

Then it becomes this super clunky, complicated – highly customized and can do everything, but I love the saying “we can do anything, but we can’t do everything.” I think many platforms, not just sales platforms, try to do everything and then businesses are trying to do it all in this platform, and it ends up never getting adopted. I think that’s one reason, just how it’s created.

I also think there’s a lack of a rollout plan that’s effective and training and really getting salespeople to see how this is going to benefit them. That to me is really key with any type of sales enablement. Anything that’s meant to help them.

ROB: And there’s only more and more tools now. More and more and more tools. You want to glue them all together, you want them to work. I think one thing I’ve seen is it seems like each organization believes that it’s unique in its needs when it comes to how they’re going to bend Salesforce to their will. Do you see a lot of customization that may not actually align with value along the way?

DANI: Yeah. It’s not even that I have to see it. I work with many businesses who say – and Salesforce is a great tool. It can do so many things, and it’s the right tool for many companies, and it’s also sometimes not, just like any tool. But what we do see is people that over-customize, and then it becomes this thing of like “we don’t even know what to do with this.”

ROB: Right, and then you get to different versions and updates and your customizations are going to break.

DANI: You need a full-time person to run it.

ROB: Yes, absolutely. You are here delivering a talk on how to build a sales play in 30 minutes or less. Let’s start with, what do you mean by a sales play, and what are we going to do with it?

DANI: My talk was on Wednesday, and it’s a topic that is near and dear to my heart. I was part of the team at our company that developed a service that we do, which is build really robust sales playbooks. So, we studied that for a good year or two before we actually built this out and started doing it a couple years ago for clients.

A sales play is really meant to, in my opinion, extract the best knowledge, the best information, everything that you need from your leadership, from your salespeople, as well as from best practices in your industry and sales best practices in general, and put that all into a process. Really simplify a unique sales scenario that a salesperson’s going to be in. It’s not about defining every single step of the sales process in one play. It’s about really this microcosm of they’re trying to identify quality prospects to call on; what are the five things they need to do?

And then really thinking through the resources and content they need. I think that sometimes gets overlooked. We can build out this play, and I’m a big believer that the content and the resources are the gas that drives it, just like it’s the gas that drives inbound marketing, that you need to create really valuable sales resources for your salespeople.

ROB: What do you do when someone doesn’t have resources and they’re not quite sure – I think it can be intimidating to think about the resources that you need to have, and in some cases it’s easy to provide something that is technically a resource, but doesn’t actually serve the customer. I think we can almost be paralyzed trying to figure out what a good resource is.

DANI: Yeah. It is hard. I think sometimes you do your best to figure it out and then you see how it goes, which isn’t anyone’s ideal scenario, but sometimes it is. It’s like, okay, we’ve created this infographic or something that we’re going to use when we’re talking to new prospects – and then you realize the salespeople are never using it. They don’t send it. Is there a reason why? Talk to them.

So that’s one way in reflection you can go back. But when you’re actually strategizing what content, I advise building out the play, building out the process and the steps, and then sitting there and looking at it. Okay, we want them to send this initial email. What would be a really great thing to send, based off of this particular persona, the research that you’ve hopefully done on them, and understanding what matters to them?

It’s piecing it in into those little gaps of the very specific – I really like to think if I could send an email to someone, what would be the dream thing? “I’d love to send them a video on this.” Okay, let’s create that video. 

ROB: Right. That makes sense. These are the different plays and you develop these different plays. Where does a playbook live? Is this on Google Drive? Is this a document you prepare as a playbook? Where does the finished product or the intermediate product, if you will, live?

DANI: This is something we’ve been really right now having conversations internally of exploring other options for this. But right now what we’ve landed on is we create ours in PowerPoint. It’s a huge deck. It’s very robust. But what we’ve found is essential is that it’s easily accessible by the sales team. We typically advise they put it wherever they normally would put stuff in the cloud. The most up-to-date version, so if that’s SharePoint or Google Drive or whatever.

The reason we do it in PowerPoint is because I don’t want sales managers not to be able to update this. If it’s in some other file or format that’s really hard and they have to rely on us that created it, that’s not fair, or a designer or something. So, I want it to be easily edited because it should be optimized and constantly added to – and ideally, in the cloud. They’re not saving this to their desktop, because it should be updated on a regular basis. So that’s where we’re at right now.

ROB: Yeah, a stale playbook is not much of a good playbook.


ROB: Absolutely. When you are first starting with a customer and they’ve engaged you, what are typically the first few things that need to happen to get them on a good, healthy path to be doing their inbound correctly, to be getting their sales systems up to snuff?

DANI: That’s one of those questions where the answer really is “it depends.” But I guess if I were to generalize, we start clearly with the website. Actually, quite a bit of the companies we work with, especially in the media space, don’t have websites because they don’t even have a B2B facing online presence. Or they have a website and it’s just not very good.

So, it’s how do we get the website ready enough for lead conversion? That’s one thing we look at. Obviously technology. Do we have the technology we’re going to need for marketing automation, CRM, things like that, and make recommendations there.

And then, really, another obvious step, but really important to us, is auditing and discovery process. We spend a lot of time really interviewing and getting to know their employees, their industry, their best customers. We do a lot of interviewing and diving deep because we can’t do our job unless we really understand what makes them different. What are the challenges they face? What are the things they’re hearing from prospects? So that’s a big part of at least our process to get up and running.

ROB: Is it hard for them sometimes to know? If you ask them what makes them special, sometimes they don’t know? “Oh, we’re nice people. We like working with each other.” Okay, but getting deeper, because there’s usually a kernel of truth there. There’s something that actually is more unique, but they just can’t name it. How do you get to that truth?

DANI: That’s a good question. Sometimes it’s really hard, because sometimes people aren’t that different. Everyone wants to be really excited and proud of their key differentiator, and some businesses just don’t have them.

This actually makes me think of what Brian Halligan said in his keynote, which was – I don’t know the exact words now, but it’s not what you sell, it’s how you sell. I’m kind of a believer in that. It resonated with me when he was talking about that, and that’s because not everyone has this differentiator. If we can find it, we help pull it out of them. I think we’re skilled in that. People are like, “Our thing is that we’ve been around for 30 years.” Like, nobody really cares, right? Or “we’re family-owned” or things like that that everyone’s really proud of, but aren’t actually important to the customer.

So, in many ways, I think it’s actually finding the message that all your competitors might be able to also say, but they aren’t saying. It’s not that you’re actually unique in it, but that you’re saying it.

ROB: Do you have an example off the top of your head?

DANI: Yeah. It might be the positioning of just acknowledging that you make your customers’ lives easier. Maybe that’s literally the point of what you’re doing. We work with a lot of PEO companies, for instance. That’s outsourcing your HR. They talk about all the things – “we’re onboarding easily and save you money and save you time,” but really, at the end of the day, people want to do that because it’s going to make their lives easier as a business owner. They need time back, and they need better benefits for their employees.

ROB: This is like TriNet, Justworks, folks like that.

DANI: Yeah.

ROB: There’s a number of them out there, and it’s one of those “I don’t want to do this” kind of needs.

DANI: Yeah, so by being able to position that “we exist to make your life easier and better,” that alone – everyone can say that, but they’re just not all saying it. They’re more talking about the service. That’s just an example that comes to mind.

ROB: There is a lot of branding that is very internally focused. You’re thumping your chest and saying how great you are to your customer without saying how great they are, or how great they can be. It’s a pretty different message. There’s a lot of selfish messaging out there. You can stand out just a little bit by speaking to the customer like a human and showing some understanding and focusing on them. That’s a different stance.

DANI: Yeah. Are you familiar with Donald Miller and StoryBrand?

ROB: Yes.

DANI: I’m a big fan and went to the workshop years ago when he first started. That just made me think of that. It’s about the hero’s journey, and you’re not the hero; your customer is the hero. So that’s something we think about a lot and pass along to our clients when we’re thinking about messaging and content development and things like that too.

ROB: Right on. Along this journey, you made the jump from Employee #2 to general manager. Was that something you thought you would do when you joined the company? Did this evolve over time and became evident?

DANI: Yeah, it kind of just evolved over time. I don’t know what I thought when I started. I had just moved to Seattle. I love this story because I interviewed with Matt as the first employee, potentially, and he didn’t hire me. [laughs] He hired the first employee. And he was great, too, so I’m sure it was a hard decision.

Then he said, “I’m going to call you when I’m ready to hire the second employee,” and I was like, “Okay, whatever,” and I moved on with my life. I actually ended up moving to Seattle during that timeframe. 9 months later is when he called me, “All right, I’m ready,” and I was like, “Okay, let’s do this.” So it was an interesting way he followed through with that.

I think none of us knew what would happen. It was a risk. It was almost like I was joining a startup within an established company. It definitely had that fun startup feeling. I think when this role came around, it was a little unexpected, but it made sense. It was a natural progression for us to grow as much as we have and to keep growing.

ROB: Very cool. You’ve probably worked in some other environments as well, so what’s the story with having a parent company? Do you have other sibling companies? What’s it like in the business family?

DANI: Our parent company, CSS, or the Center for Sales Strategy, is the largest part of our company. There’s also a sister company that’s brand new called Up Your Culture where we’re really focused on helping companies with improving their company culture and employee engagement, so that’s a really exciting, cool thing. We think we do a really good job of it, so again, we said, “We should help our clients with this.” That’s kind of how we roll, I guess. So that’s the three companies.

We’re all very intertwined, though. We share resources from an administrative level and things like that. We share a marketing department, accounting, HR. But otherwise we’re running pretty separately. But our cultures all intertwine. Biannually we have an annual staff meeting with everybody. We do monthly culture calls with everybody. So there’s nice cohesion, but being totally remote, there’s people who never actually work together. But everyone seems to get to see each other’s faces on video and things like that.

ROB: People really, from a cultural perspective, like that. You have to have a degree of trust to be so remote. You get some flexibility in life. You have a bunch of people who aren’t mad about commuting. There’s a lot of good stuff in there.

In the years that you have been growing with and building LeadG2, if you were starting from scratch today, what are some things you might do differently upon reflection?

DANI: The first thing that comes to mind, because I was actually just talking about this with Matt earlier this week, we would’ve charged more sooner. We wanted to build up our own confidence, and for us, we wanted to make sure we really could get results for our clients – and we did, really quickly.

So, we probably could’ve raised rates quicker than we did. I think there was just that – we started doing more, because the more we learned, the more we were able to do. When we were in the really early stages, every month we were drinking from a water hose of what we were able to do for our clients. We just kept doing more and growing out of scope, even though we weren’t charging them more. So that happened.

And then even over the first few years, it just took a while for us to catch up to where – I still think we underprice a little bit. [laughs] But yeah, that might be a big one, I think.

ROB: What are the signals, other than being really busy, that signal to you that you may be underpricing?

DANI: This is a really positive signal, but just getting lots of results for our clients and really high retention rate. We’re really proud of our 80%+ retention rate right now. We do annual retainer clients, mostly. So that’s really a great sign that we’re doing a good job and that there’s opportunity to continue to build on that and attract even more companies.

ROB: You have visibility more than most companies a client might work with. You have much visibility into the results. You know we’re driving dollars XYZ into this company, so you know maybe when you’re producing a lot more than you’re charging.

DANI: Totally, yeah.

ROB: How has your role shifted in the company? What do you find yourself spending your time on?

DANI: To be real honest, it’s been an interesting ride the last couple years being the general manager in this role. My number one goal when I stepped into this role was to really take everything off of Matt’s plate. He’s the managing partner of the entire company, so for him to get his focus back on other things and not have to – I mean, he’s still very involved, but that was a big transition.

Managing the people. That’s probably the most important thing I do. I care so much about our employees and that they’re growing, they’re satisfied, they feel like they’re able to perform and have what they need. I also manage our sales team. We have two full-time salespeople at LeadG2, so that’s another adding on.

And I continue to be a lead consultant with some of our clients. That’s something that I really love that we do in our company. Our two managing partners, Matt Sunshine and John Henley, both also still are consultants on accounts at CSS. It’s just a belief we have that you can’t be a great leader if you aren’t really in touch with the needs of your customers and you’re there.

There’s always that balance of being a leader, strategizing, managing, coaching people, and then also still doing client services. And it ebbs and flows, depending on – when we’re a little tighter and ready to hire but not quite ready, I pick up the slack for my team and fill in the gaps of client services. Then I can spread it back out, or training.

Where I’m focusing my attention definitely ebbs and flows month to month. Right now, I’m doing a bit more client services. We’re recruiting. We’re hiring for two jobs right now, so that’s part of that, those in-between stages when you’re still a pretty small company, growing.

ROB: As you’re looking ahead, what are some of the adjustments you think that people are going to need to make to their sales plays, to their technology stack? What are the adjustments coming up this next year?

DANI: Let’s see. The adjustment would be actually the implementation. I think more companies are realizing – it blows my mind how many companies don’t have a sales process or sales strategy, like nothing even barely in writing. It’s like “go out and sell, here’s this deck,” and that’s it.

I think more and more – and especially companies that are doing great marketing and great lead gen, and yet they don’t have that structure on the sales side. I think that’s part of it. Or it’s the opposite. They have this great sales structure, but they’re relying 100% on outbound. To me, balance I guess would be the answer, that alignment and that balance.

And then there’s the obvious things I see of just more businesses realizing the value of video and needing to do that and investing in that. I think people also are starting to really – there’s a lot of companies that pay for CRMs and don’t really use them. We come across that a lot. They use it as like an account list management, and that’s it. So, I think people are evaluating, “Is this the right CRM? Are we using it? Do we need it to be this complex? What is really the most important thing?” In my opinion, it’s: is this helping your salespeople sell more?

ROB: You sit in a place where you have perspective on what’s working across a lot of people. It helps when an organization is thinking about what kind of metrics are going to contribute to success in a role – is this the type of industry that is going to take some more personalization, less personalization, what channels are going to be effective?

There’s also a lot of hearsay and rumors over what works and what doesn’t. To hear clearly that video – this is like a Vidyard/Loom type of thing where you’re recording a custom video and sending it out to a prospect?

DANI: Yeah. That’s something we really believe in, and we’ve seen, again, tested on ourselves and had a lot of success in the early days with Vidyard and integrations and things like that. Big believers in personalized, a salesperson just shooting a quick video.

But also, I think professionally shot videos too. Having really strong case studies and success stories on film. “On film.” [laughs] I don’t know what year it is. But yeah, I think it’s a mix. I think it’s having those more high-end videos that they can use, and then those little quick cuts and them being able to easily film their own stuff.

ROB: For some of the other outbound channels, what’s the truth? You hear some people say phone calling doesn’t work anymore, and you have other people say the people that don’t think phone calling works anymore just don’t like phone calling, so they don’t do it. Whether you’re talking about social selling, email, phone, is there any real trend or change in effectiveness? Or is it kind of the same as it’s been?

DANI: I’ll tell you, we’re still big believers that you’ve got to pick up the phone. It works differently than it used to. You’re not catching people on the phone. People are not answering from random numbers. It’s a lot easier to not answer, to ignore people.

But we do believe – I’m mostly speaking, obviously, to the B2B space here – that that needs to be incorporated into the sales process for sure. Phone, email. Leave voicemail, follow up with an email. Just those different touchpoints, because you don’t know who you’re talking to and you don’t know their method.

I sit there and I talk to my friends – I have a lot of long-distance friends, and some people love talking on the phone and some people hate it. Some people want to email, some people want to text, some people want to video chat. We can’t ignore that people have different ways they like to communicate and consume content and all that. And social, of course. We’re big believers that utilizing LinkedIn in particular in that approach stage is really valuable.

ROB: This is connecting? Are you customizing the message or not? Is that trending either which way?

DANI: I think yes, personalize the message. For the industries that we work with.

ROB: Dani, when people want to find you and when they want to find LeadG2, where should they look to find you?

DANI: You can find LeadG2 – we’re on Twitter, all the normal places, Facebook. LeadG2, just like it sounds. And You can find me on Twitter. That’s @daniobuckley, and I’m also on LinkedIn.

ROB: Perfect. Dani, thank you for coming on the podcast. Thank you for dropping some sales knowledge. We appreciate it.

DANI: Yeah, thanks for having me. Nice to meet you.

ROB: Likewise.

Thank you for listening. The Marketing Agency Leadership Podcast is presented by Converge. Converge helps digital marketing agencies and brands automate their reporting so they can be more profitable, accurate, and responsive. To learn more about how Converge can automate your marketing reporting, email, or visit us on the web at

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