
Sales Enablement Innovation · 2025-06-13 · 19 min
Grace McCann, with a decade of experience in cybersecurity and AI SaaS companies and a master's degree in adult learning theory, argues that enablement is uniquely positioned as a second or third touch point to shape company culture for new hires. Rather than treating onboarding as purely transactional checklist completion, she advocates weaving company values and cultural tenants directly into learning experiences - from welcome calls through ongoing coaching. Her approach balances the urgency of sales ramp-time metrics (reducing time to first deal, increasing deal size) with genuine culture-building by selecting onboarding ambassadors who demonstrate authenticity, warmth, customer service mindset, and respect for employees' personal lives. McCann shares practical tactics like asking new hires why they joined the company, displaying personal calendars showing work-life balance in action, and using phrases like "progress over perfection" to embody values. She emphasizes the "build once, scale many" philosophy - identifying which learning can be shared across presales, sales, and post-sales roles versus what should be role-specific. Sustaining culture beyond initial onboarding requires partnership across leadership and consistent reinforcement of cultural practices over time.
Start small by explicitly stating values and mission on the first welcome call, then weave cultural tenants into everyday coaching conversations and talk tracks. This approach embeds culture authentically without adding separate activities, allowing you to maintain ramp velocity while building belonging and engagement.
Look for people who demonstrate authenticity, warmth, and a customer service mindset toward new hires; avoid those solely focused on checking boxes. Ambassadors should balance advocacy for the new hire with accountability to learning objectives, and respect employees' personal time and life outside work.
Be considerate about scheduling, avoid overwhelming activities or unreasonable hours, and openly model work-life balance by sharing your own calendar with personal commitments. Show that the company genuinely respects employees' whole selves, not just their desk time.
It's a scalability strategy that uses a Venn diagram to identify which learning experiences can be shared across presales, sales, and post-sales roles (like company culture) versus what should be role-specific. This maximizes cultural immersion while maintaining efficiency across regions and time zones.
Strong onboarding builds employee confidence, buy-in, and engagement from day one. New hires who feel welcomed and aligned with company culture are more likely to stay longer, perform better, and ultimately drive revenue - making culture-focused onboarding a direct investment in the revenue engine.
Computed from the transcript - who did the talking, and the words that came up most.
On this episode, we spoke to Grace McCann about how enablement can use its position as an early touchpoint to build a positive company culture straight from onboarding. Key talking points: Enablement as a culture-setter What the role of onboarding ambassador entails Balancing ramp-time urgency with culture-building And more!
Transcribed and scored by The B2B Podcast Index.
Speaker A: Welcome to the Sales Enablement Innovation Podcast brought to you by the Sales Enablement Collective. Each episode we sit down with sales enablement and revenue leaders from around the world and invite them to share their expertise and experience with the community. On the show today is Grace. Grace, thank you for coming on and welcome to the podcast.
Speaker B: Thank you. I'm so delighted to be here.
Speaker A: So before we jump into today's episode, could you give a bit of a run through of your background, introduce yourself for our listeners and just let us know what you've been up to in enablement so far?
Speaker B: Sure. So I have, um. Well you know what, first let me introduce myself. My name is Grace McCann, um, and I've spent the 10 years or so at Ah, cybersecurity and AI companies, um, mostly SaaS and PaaS, preparing the field for sales success. Uh, so in my last role I owned a global field onboarding program for both pre and post sales team members where I was responsible for creating role based onboarding experiences that could then scale over roles, regions and times time. I uh, couple that experience in tech sales enablement with a foundations in adult learning. So I've got my master's degree in adult learning theory, um, and I use those two, two things to produce engaging and impactful learning experiences. Um, I would say my greatest joy at work comes from seeing one of my new hires earn their way to that president's club stage.
Speaker A: I love that. And that's such an awesome background to have in enablement. You've got the perfect mix, especially with the adult learning. It's such a key part that sometimes isn't really talked about as much. Ye, um, and so today we're talking about enablement's role as a culture setter and the idea that ah, enablement kind of has a responsibility to be a culture setter as one of the first touch points for new hires before we sort of dive in super deeply into it. Could you explain why you sort of feel strong about this sort of culture setting idea and culture setting responsibility that enablement has?
Speaker B: Yeah. So if you think about enablement organizations in a lot of companies they are oftentimes maybe the same second touch point or the third. So sometimes somebody's recruited by their past manager, so that's number one. Then there's the second one with recruiting and then here comes enablement, um, with this huge journey and experience. And what got me feeling so strongly about this is I had a really good onboarding experience um, in my first inside sales role. That program manager was energetic. She really made learning Fun and embodied the company culture. When I graduated from that um, training program, so to speak, I felt really confident in my role and that made a lasting impression on me. Uh, so now fast forward a couple decades, uh, and now I'm the one preparing new hires for the field and showcasing that link from my onboarding programs to increase revenue and improve retention.
Speaker A: I love that. And something you mentioned there as well, we chatted about before recording as well, is that you onboard pre sales, sales, post sales, like there's sort of a bit of everything in there. Does how you set the standard culture wise differ between those sort of functions or is it kind of a unified approach? You go at it all at once? How do you sort of, yeah, I guess separate or attack those sort of different areas.
Speaker B: So I take a unified approach with this. I'm a big believer in the build once model, so I'm always thinking about scalability when developing onboarding programs. Part of my strategy is to think about this Venn diagram of where a, ah, learning experience can maybe be shared across roles and where it should be more role based. And I think company culture is an experience that is so much more fun when we share it across roles. So for example, when I'm hosting an onboarding session, one of my favorite questions to ask new hires is why did you join this company? The responses you get from this Daniel are fantastic. I've heard all kinds of things from the technology is great to pay in benefits, which of course is important, and opportunity for growth. But when the answers are repeatedly things like I followed a previous leader or they say things like the people or the culture, you know that you're really doing something right in the way of the people and the culture at your company?
Speaker A: Uh, uh, I love that. And I guess the follow up to that is how do you balance the need for sort of ramping new hires asap? That sort of urgency, that's a sort of sales and SaaS world brings with sort of culture building and sort of maybe slower burn ideas like that. Where do you sort of. I'm sure people at home are listening thinking, yes, that's great but I got these targets to hit and you know, the ramp time has to be super quick. How do you sort of, I guess balance all of that and sort of make it all mesh together really nicely?
Speaker B: Yeah, that's a great question. And this part definitely takes some brainstorming and creative thinking. I want to keep my audience's onboarding goals in mind, of course, because that's the core of my job. Right? My job if we take it to the AE side, for example, I'm focusing on things like reducing ramp time, increasing their deal sizes and decreasing time to deals. Uh, so if I'm hosting an early discussion about why they joined the company, I craft my response in a way where I can incorporate a company value. Now it is of course important to be genuine, so I pick a value that really speaks to me personally. In the past, I've gotten another example. There was a cultural tenant where, uh, they encourage us to focus on continuous improvement and reiterating and improving versus instant mastery. I think a lot of times we want to jump in and be so good at our jobs, but it takes a lot of practice. Uh, so this one, of course, as a learning practitioner and as an enablement practitioner, it really spoke to me. Uh, so how does this translate to onboarding? Or how do I brainstorm to get this into onboarding? I use it as part of my talk track and I try to get those value tenants in the way that I talk. So if I notice someone doesn't feel confident, perhaps in their pitch practice or they're down about an objection handling response, I coach them and show them what good looks like. But then I also remind them that we're all new, we're all learning, and what we're ultimately striving for is progress over perfection. Um, so I try to build in the values that way. And in the end what I find is it's important that I personally understand, believe in, and embody that company culture myself. I think if you don't have a genuine connection to the company culture, it's hard to cultivate that in your new joiners.
Speaker A: That makes a lot of sense and I really like that sort of progress over perfection as well. Like, that's a, ah, that's a great way of phrasing it and um, I appreciate that. Um, um, I guess for listeners who are reflecting on their own onboarding programs right now and thinking maybe they're not doing enough of that sort of instilling the culture. They haven't been doing that brainstorming. What advice would you give them to? Where do they start? Because m. Maybe it can be a bit overwhelming to think about doing it all at once. Like sort of, uh, what you mentioned there. For people who are starting this sort of culture setting journey, what advice have you got for them?
Speaker B: Yeah, I would say the same as my motto and that start small and scale. Right. So find an early place somewhere in the onboarding. Maybe that first welcome call where you explicitly state the company's Culture. So you're going to state the things like the company's value, missions and vision, or maybe you have some sort of culture code or tenant or something like that. I find that showcasing that right up front helps to frame their mind and how we behave here, how we treat each other, things like that. Um, and then from there, I'll ask the audience for some engagement, and I'll ask the new joiners how those things resonate with them. And this is, again, where you get a lot of interesting ideas, uh, across roles, across regions. And I find that this helps the new hires connect with each other. And that's part of that culture too, right. To get embedded and feel like you belong at this company. Um, so I like to ask that question. From there, I think of ways that the organization practices or even displays the values. Right? So how can we see some of these things in practice? And one thing that I did in a past role is I think of this cultural tenant that talked about work life balance and the flexibility that we had to take care of our personal commitments. This company was known for saying, take a nap during the day if you need to refresh, um, or, you know, do the things, even if it's during traditional working hours. They really respected us to take care of our life and take care of the role that we committed to. Um, so I would bring up my calendar, right? And on my personal calendar, I had things like kid pickup, dentist, or a lunch date with a friend. Um, and I'd show them my calendar and talk about that flexibility that we have, because I do think that sometimes it is unique. And then I'd strongly encourage them to keep the routines that were important to them. I would say things like take your nan out for lunch or go and, you know, do your physical therapy or have that walk, if that's something that is important. What I found is that as you're building those cultural touch points into your onboarding, it's vital to be really respectful and mindful of that new higher schedule and personal lives. Right? We want to retain them and ultimately make them feel like they made the right choice. So while I want to immerse them in the culture, overwhelming them with too many activities or scheduling things that are outside of reasonable hours can have the opposite effect. So I want to make sure that I'm considerate of their time and commitments, um, and make sure that they understand that we respect their whole selves, not just their lives behind their desk, and build that connection with them in a much more positive and sustainable way that
Speaker A: makes a Lot of sense. And I guess following on from that is something that I think we spoke about as well before recording is we mentioned this sort of onboarding ambassador role, um, and that sounded sort of really important to, um, what you were trying to do. Um, I guess before anything else, can you sort of, I guess, describe that for a little bit and what you sort of have in mind when you're picking out an onboarding ambassador or I guess, what that means to you as a whole?
Speaker B: Yes. So this is one of those things that is more of a Persona. Right. So sales be familiar with this. It might be the onboarding program manager, but it might also be your mentor or anybody that's really helping this journey, to facilitate this journey and this experience through onboarding. So it may be some of the presenters, um, things like that. So when I think about the onboarding ambassador, these people have got to be people that also show the company culture in different ways. I think that they are a true linchpin in making those early experiences positive and culturally immersive. So when you select those people, I look for a couple red flags or pitfalls, so to speak, to avoid. And one thing that I think is really important is having this customer service mindset applied internally. So if you think about it, our new hires, they're my internal customer, right? They're the ones that I'm providing value to. So I want to make sure that I'm supporting them and giving them a positive experience from the get go. Uh, so a red flag might be someone who's solely focused on checking the boxes and completing the onboarding tasks without maybe, uh, worrying about the feel of it. I think another crucial element that kind of blends into that as well is warmth, openness, and genuineness. People are incredibly perceptive, especially salespeople. Right. Like, we are trained to understand what our, uh, the other side of the call is thinking and how they're behaving. Um, so when I think about that, if an ambassador isn't authentic or doesn't genuinely enjoy connecting with and supporting those newcomers, they can possibly feel that, uh, and we don't want to do that either. And then that, uh, really drives me to something that we touched on a little bit earlier. And that's a lack of respect for the new hire's time and personal life. So it is true that sometimes sales reps will go across continents for an onboarding workshop. Perhaps we're doing it virtually no matter what the format is. I want to make sure that I'm always respectful of that learner's Time. And I've heard comments in the past about owning a new hire's time during onboarding. And I think that's really detrimental and completely misses the point of building a positive and sustainable culture. Um, you want ambassadors that are going to be advocates for the new hire and understanding that they have lives outside of work and ensuring that that onboarding process is respectful of those commitments. Um, and finally, it's important to ensure your ambassadors can follow or balance their advocacy rather for the new hire with the overall goals. Right. So I want somebody that's not only focused on being a friend and overlooks the critical learning objectives, but I also want somebody that can blend the two. So I'm looking for somebody that can, um, support and guide and be a champion for that onboarding process, but also make sure that they're fitting in and ultimately set up for success in their role.
Speaker A: I love that those really in depth. Thank you loads for our listeners to go off. And I think that authenticity point is so important as well. People can really. They can smell when someone's being inauthentic. Right. So it's key to be able to sort of have an authentic figure there. Um, I guess beyond that sort of formal onboarding period that we're all sort of familiar with, how can companies sort of ensure that cultural integration and learning mindset is. That was established early on is like actually sustained and reinforced throughout an employee's journey. And it's not like a thing where you get it in the first couple of months and then it's never spoken about again. How do you, I guess, make sure that that is actually a sustained, uh, effort from everyone sort of involved?
Speaker B: Yeah, I think this takes a partnership and deep relationships and trust across the organization. So to keep it going. Um, for, for starters, the one of the things I do in early calls when I'm welcoming on ah, or rather welcoming new hires, I'll say, hey, I know you might not know this yet, but we're a camera on company here. So if you're camera ready, I'd encourage you to turn your camera on. If you're not, that's okay too. And what that does is it kind of clues them into the culture for the long term is I should maybe be camera ready and, you know, uh, brush my hair or whatever it may be today. So I think think we do that and then just keep reiterating those things. Right. A lot of us, especially having been through the pandemic and switching to this virtual world, we do get fatigued on camera. We do get fatigued with too many activities and things like that. So when we think about embedding culture in the long term, I think it comes with setting up a foundation early and then to keep coaching and mentoring and building that through the leadership and the other organizations where we're all kind of embracing it and then, um, embodying that.
Speaker A: I love that. I love that. That makes a lot of sense. And I guess before we wrap things up, would you be able to sort of tie it all up in a bow in if listeners could only take one thing away from this episode, what should it be? What's your golden nugget of advice that you would give to anyone who's sort of really trying to drive culture integration into their organization? Maybe they're in the early stages, maybe they haven't started yet. But what's the sort of key takeaway from your experience in being this culture setter?
Speaker B: Yeah, so I think from my experience in being a big part of that early onboarding side is that culture is one of, or I'm sorry, onboarding rather is a prime opportunity for us to intentionally cultivate the company culture and directly fuel our revenue engine. We can't underestimate the power of those initial first days and weeks and what it means to a new hire in their buy in and their eventual success in the company. So if we thoughtfully weave our values into the onboarding experience and empower our people to champion that culture, we're not just welcoming the new hires, but we're really investing in a more engaged and more productive and ultimately a more profitable future. So I think if I could tie it up in one sentence, what I would say is really think about how you weave the culture into, uh, your programs and then that will help to continuously perpetuate and drive that positive culture at your organization.
Speaker A: I love that. Really make it a deliberate choice. Uh, and starting from there. That's really great advice and I think that's all we have time for. But thank you so much, Grace, for coming onto the show and sharing that. I really enjoyed that and I think there's some really key points that people will be able to take away from that. So thank you for coming on and sharing that and it is really much appreciated.
Speaker B: Of course, Dino, it was so nice seeing you again. And until next time, thanks for tuning
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