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Leading Sales Success Through Culture and Tech Innovation – Jason Grimes, VP of Sales

Join Jason Grimes from Stretto is making a career change. He combines strong Corporate Restructuring legal skills with sales know-how. He joins us in our latest Sales Lead Dog episode. Jason shares his fascinating journey. It weaves through the labyrinth of bankruptcy and corporate restructuring.

He demonstrates how leveraging his legal background has been a game-changer in his sales strategy. As the VP of Software Sales, he reveals a crucial insight. Understanding the exacting needs of legal professionals has not only honed Stretto’s offerings.

It has also reinforced his credibility and effectiveness in a market where precision is paramount. This highlights Legal Tech Sales Leadership.

Building Authentic & Resilient Sales Team Culture

Building an authentic and resilient sales team culture is truly an art. Jason paints us a vivid picture of how he achieves this. With a player-coach approach and a strong emphasis on vulnerability, he creates an atmosphere.

This atmosphere encourages genuine interaction and confidence. He also throws in a unique meeting tip. This helps his teams segue into discussions with ease and authenticity. Jason’s insights are a masterclass.

They cover nurturing a sales environment that aligns with company values. At the same time, it fosters individual growth and collaboration.

Tech as the Backbone: CRM & Sales-Marketing Integration

Technology isn’t just a buzzword for Jason; it’s the backbone of operational success. Through anecdotes and expertise, he unwraps the importance of a robust CRM system. He also discusses the art of conducting nuanced job interviews.

Furthermore, he explores the intricate dance of integrating sales and marketing technology. This episode doesn’t just scratch the surface. It’s a deep exploration into creating a synchronized ecosystem. Here, sales and marketing technologies work in concert. This offers a glimpse into the future of strategic business growth.

Tune in to discover how Jason Grimes orchestrates the symphony of sales, legal tech, and leadership.

Meet Our Guest: Jason Grimes, VP of Sales, Stretto

Jason Grimes is a seasoned leader. He has over 20 years of revenue-generating experience in the legal technology industry,also boasts a proven track record of success. He has a long history of building and leading strong teams. This experience gives him practical skills for his role at Stretto.

He leads the organization’s business-development efforts for its Best Case by Stretto business unit. Jason understands the importance of serving as a trusted partner to clients. He is passionate about helping law firms achieve their business goals. He does this by leveraging technology resources to maximize productivity. As a licensed Attorney, he is a recognized legal-technology expert.

He has been featured in publications such as The American Lawyer, The National Law Journal, and Law360. He is also a frequent speaker at industry events. Before joining Stretto, Jason held various senior positions with LeanLaw, AbacusNext (CARET), and Aderant.

Key Takeaways You’ll Learn:

  • How legal expertise can be a game-changer in legal tech sales strategy.

  • Strategies for building an authentic and resilient sales team culture.

  • The importance of vulnerability and a player-coach approach in sales leadership.

  • Insights into leveraging robust CRM systems for operational success.

  • The art of integrating sales and marketing technology for strategic business growth.

  • How Stretto addresses the needs of legal professionals in bankruptcy and corporate restructuring.

0:01
Welcome to the Sales Lead Dog podcast hosted by CRM technology and sales process expert Christopher Smith.

0:09
Talking with sales leaders that have separated themselves from the rest of the pack.

0:13
Listen to find out how the best of the best achieved success with their team and CRM technology.

0:20
And remember, unless you were the lead dog, the view never changes.

0:27
Welcome to sales lead dog.

0:28
Today on this episode, I have Jason Grimes of Strato joining me.

0:33
Jason is the vice president, software sales for Strato.

0:37
Jason, welcome to sales lead dog.

0:39
Thanks, Chris.

0:40
Good to be here.

0:41
It’s great to have you here, Jason.

0:43
Jason, tell me a little bit about Strato.

0:46
Sure.

0:47
So Stredo is a company that works all across bankruptcy and fiduciary concerns across the entire bankruptcy ecosystem from trustees to corporate restructuring to selling software, which is division that I lead to consumer bankruptcy attorneys to help individual debtors.

1:11
I imagine that is, you know, people think bankruptcy, you know, how big is that or whatever.

1:18
But I would imagine especially when you get into corporate bankruptcy, that’s pretty big, pretty complex cases.

1:23
Is that where straddle comes into play to help deal with that complexity?

1:27
For sure, for sure.

1:29
We have a corporate restructuring side that helps out with like everything related to claims and noticing and kind of a little bit of behind the scenes stuff that the big major corporate law firms do along with the creditors.

1:42
For example, the Neiman Marcus Bankrutcy from a decade or so ago.

1:46
All the things related to getting noticing out to all the different creditors, dealing, all of the due diligence work behind the scenes.

1:54
Those are the kind of things that we do on that side of the business.

1:57
And frankly Stredo was founded about six years ago coming together of three different separate entities that worked in the bankruptcy world, all came together, new corporate umbrella called Stredo was created, but they kind of came out of pre-existing entities in my world.

2:14
And again, I live mostly in what we call the debtor attorney space.

2:17
In other words, attorneys who work with the debtors or the consumer.

2:21
Bankruptcy space is another way to put it.

2:24
The brand that’s really well known amongst that world is a software platform called Best Case.

2:30
And so, you know when you go to see us at conferences, it doesn’t just say Stredo, it says Best Case by Stredo because that’s the brand that’s best known.

2:39
You know, I’m sure you’ll ask questions about it, but I’ve got 20 years history of working with software in the legal space and I’m also a lawyer by training, so I’ve kept my license up and all that stuff.

2:51
That’s wild that you’re the 1st licensed attorney I’ve had on the show.

2:56
So well, don’t ask me for any legal advice, but we’re all good.

3:02
But you are licensed and able to give it if needed, right?

3:04
Well, in Ohio and we’re recently I stayed practice.

3:07
I know you’re in Colorado, so I’d have to kind of say I’d have to like do all the all the caveats and all the disclaimers around this is just shame tree advice.

3:15
You know, we’re just talking about the water cooler.

3:18
So you went to law school.

3:19
I’m sure when you went to law school, you weren’t thinking, hey, the hell with the law, I’m gonna go into sales.

3:25
How’d you get into sales?

3:27
It’s interesting.

3:28
I kind of did everything backwards.

3:31
And so if anybody takes anything away from the from from this at the kind of the personal story level, I think it’s important to know that there’s not one right way to do things.

3:41
There’s not a trajectory that makes sense for everybody.

3:44
My trajectory to where I am today, mid career, if you want to call it that, is a little backwards for a lot of, you know, people even in my industry.

3:53
I was recruited to work for LexisNexis, which a lot of people will have heard of, while I was just kind of petering through life, just, you know, selling insurance, leading a small team in the insurance business.

4:05
LexisNexis came calling and I wanted to kind of move towards more of AB to B world as opposed to closer to AB to C selling benefits and stuff like that.

4:14
And so I went to LexisNexis and started talking to all these lawyers and I was like, you know what?

4:19
This is intellectually curious to me and also an area where I could see myself kind of doubling down in a niche, if you will, for my career.

4:29
So while working at LexisNexis, I went to law school at night here in Cleveland and, you know, made law review, was able to take a three month leave of absence and go kind of, you know, at least, you know, not chase that dream, but just kind of see what it’s like on that side of the desk.

4:47
So I did a three month internship.

4:48
It’s called summer associate in the legal world.

4:52
And frankly, you know, ended up coming back over to this side, over to the technology sales side because I think it matches up to my skill set best.

5:02
And, and it just, it just seemed to make sense for me career wise.

5:05
And I’m, I, I don’t regret it for one day, but I have kept my license up because I did go through all the hassle of getting the degree and passing the bar and all that kind of stuff.

5:13
Oh yeah, no, I was going to say, like you do all that work.

5:17
You know, I used to work in the healthcare industry a lot and occasionally come across doctors that a very similar journey as yours where they, you know, went through all the pain and the time to get that to, you know, to achieve that and then to not keep it up would just seem like a waste.

5:35
But I think that’s pretty cool.

5:36
You’ve done that.

5:38
Yeah.

5:38
It’s credentialing.

5:39
You know, I mean, I work with lawyers every day.

5:40
I talk to lawyers every day or my, my team now, now that I’ve been in management for about 10 years, more or less.

5:48
But you know, we work with lawyers every day.

5:50
And so having somebody that understands, you know, rules of procedure and rules of evidence and how cases kind of move through the system, you know, having that has certainly been helpful.

6:02
You know, I’m a big believer in, in a salesperson, whether they’re the person knocking on doors or first level management, second level management, huge believer in them bringing a ton of subject matter value to every conversation.

6:17
I treat sales and sales leadership really or sales in particular, as being kind of like a short term, narrowly focused consulting more than how can I get you into these, you know, bucket seats kind of thing.

6:29
So, you know, when I, when I talk to my salespeople, I, I kind of tell them how right.

6:34
I, I kind of like teach how to kind of guide people through a process as if you’re a consultant rather than push the people through a process like you’re a salesperson.

6:46
So you’re bringing that expertise as a lawyer and then being able to kind of impart that to my team and, you know, kind of have that, you know, I belong in the room kind of sense is really important.

6:57
So what was your motivation to go from being a salesperson, carrying a quota or all that to shift into a leadership role?

7:06
That’s a really good question.

7:08
I have been in both sales and leadership roles going all the way back to college and I really enjoyed being in sales leadership, recruiting, managing, training, teaching, motivating, inspiring, all those kinds of things going all the way back to college.

7:26
Chris, I don’t know if you’ve ever run into anybody in your journey of, of talking to hundreds, if not thousands of, of sales leaders, but I was one of those guys that ran around in college selling books door to door, like in neighborhoods.

7:39
Have you ever run anybody that did that?

7:42
I interviewed for a job selling knives.

7:45
And then once I heard what it was, I, I didn’t move forward with that because the whole thing was like, this is not a job selling and we get in there and like, Oh, yes, it is.

7:54
Yeah, yeah.

7:54
That would be Cutco.

7:56
I Cutco exactly or whatever.

7:58
So, yeah, that, you know, I’d rather sell books than knives door to door, whether it’s the 90s or the twenty 20s, you know, there’s something but, and frankly, I probably wouldn’t do it in this day and age, but back in the 90s, you know, I, I put myself through college selling and then recruiting A-Team.

8:13
And by the time I was done with college, I actually had an organization of over 40 people that were kind of organically under me in kind of that.

8:22
I’m not going to call it multi level, but but you know, you recruit people and if some of those people do well, then they come back the next year and recruit people.

8:28
And that’s how I built that organization.

8:31
So I think I was probably cut out for for some type of leadership, you know, you know, for my career, it took me frankly, 10 years in legal tech.

8:43
I’ve been in legal tech for about 20 years.

8:44
It took me 10 years of carrying the bag and then the right opportunity came along for me to move into kind of a regional sales director with a team of about 5 people.

8:55
Then that grew into, you know, promotion, if you will, to national director of business development, team of about the same number of people, but just spread out over the whole country and focused on a particular customer profile, if you will.

9:11
And then, you know, from there it’s just been leading small to large.

9:15
So, you know, my largest teams I’ve LED have been around 30 people with three managers and a, and A and a layer of, of account executives as well.

9:25
So from anywhere from 3 to 30 people over the last 10 years I’ve been leading, managing, recruiting, training and all of it.

9:35
So I think a big part of being a successful sales leader is creating a culture that aligns with the core values of the the company.

9:46
What’s your philosophy around how you go about building that culture within your sales team?

9:53
Well, you know, every company has has great core values.

9:57
You know, I’ll I’ll read one of them I keep on my screen here.

10:00
One of them for our company is to go above and beyond, save our clients and each, I’m sorry, serve our clients and each other with responsiveness, respect and enthusiasm.

10:11
That that probably sounds like a core value that that there’s something like that about being customer centric, for example.

10:18
That would be a core value that probably anybody listening to this would would have, you know, similar core values for their company.

10:25
One of the core values that has really worked for me a lot in the in, in the over the years is to really focus on the internal sale.

10:35
By internal sale.

10:36
What I mean by that is when you’re, whether you’re a account executive, you know, an individual contributor, first level manager, second level manager.

10:45
If you can’t make that sale internally to be able to either get the discount that you want or the special, you know, way to package something up if you’re a Rep or to be able to advocate for a particular position or go to market strategy.

11:00
If you’re a manager or AVP.

11:02
If you can’t make that sale internally with all the different stakeholders, that’s going to be a problem because you’re put on an island, your, your sphere of influence is really minimized.

11:12
And so I’ve worked very hard to, you know, build up rapport and positive culture with the people that I work with at both the peer level as well as, you know, in any hierarchy, if you will.

11:24
I’m not a particularly hierarchical person, but but you know, there’s layers of management just like anywhere.

11:31
And so if you build up good relationships vertically and horizontally, and the only way to do that is through mutual respect, honesty, just kind of being real, bringing your real self to work, people can tell a fake a mile away more and more so.

11:49
So if you’re not real or if you’re just kind of giving a line or if you’re kind of putting on airs or trying to, you know, kind of pump like like aggrandize yourself at the expense of the team or the company or, or the the service that you’re trying to provide internally and externally.

12:07
People can see through that and, and, and nobody’s impressed by that kind of stuff.

12:12
No.

12:13
What role does vulnerability, not only for you, but what amongst your team play in, in building that culture?

12:21
Well, that’s a good question.

12:23
I, I think that when you say vulnerability, another way to just kind of put that is just realness.

12:32
Look, I don’t expect my reps or my peers to bring all of their gripes and all of what happened bad to them over the weekend to the office.

12:41
I think that can go too far in a certain direction.

12:44
At the same time, we’ve probably all been in meetings before where we feel like there was somebody in there that just kind of sucked all the energy out of the room or sucked all the air out of the room because it was just like everybody’s on pins and needles walking on egg shells.

12:57
When’s the next shoe going to fall?

13:00
This person is in here and they’re here to kick **** and take names and just kind of show that they’re, you know, that they’re boss and that they’re tough and, and that kind of thing.

13:09
That type of culture never motivated me as a Rep and, and I’m thankful that I was that I carried the bag arguably for 10 years in legal tech.

13:16
But even before that, whether it’s in the insurance business, I was AI was a, a player coach in the insurance business and I was a player coach even going back to College in the book business, you know, as a college student.

13:28
So I’m a big believer in that player coach model and that has really informed my my approach to sales management.

13:36
I guess you could say that I’m kind of a reps manager or reps VP.

13:40
I don’t come from a top down approach, but I come from an approach of what would I want if I was a Rep to be able to be empowered, to be able to succeed.

13:50
And so that’s what I try to bring to a team is that now when you’re in a meeting, then you know what’s a practical thing?

13:57
A practical thing that that I’ll do at the beginning of all my sales meetings is have something that I call Segway might have heard that used in this concept before.

14:06
And yeah, it kind of comes from some business principles that they get bandied around.

14:10
But a segue is where we take ourselves from wherever we were, whether we were working on a spreadsheet or just had an uncomfortable conversation with my with your partner or an uncomfortable conversation with another colleague.

14:20
It’s it’s where we just kind of clear our mind and get present in the moment for that meeting.

14:25
And the best way to do that is not to just rip the needle off the record and go straight into, OK, let’s talk about deals.

14:32
Best way to do that is to give a two or three minutes on kind of what’s going on in your life.

14:37
And so over the course of a year of doing that every week in a sales meeting, you’re going to learn that that person is a is a whole person is a complete person.

14:45
What they’re into, Are they into fishing?

14:47
Are they into golf?

14:48
Whatever it is, you know, is there a kid looking at college?

14:51
These are the kind of things that help you kind of keep that room more open and collaborative and to use your word vulnerable, I guess again, that’s a word that maybe is a little bit more emotionally charged than I want it to be because you don’t want to, you know, I have a big belief you never dump down.

15:11
You always dump up.

15:13
So, you know, like I would never go to one of my reps and be vulnerable in a way that’s inappropriate.

15:18
That just is like, man, this guy’s just a, you know, a complainer or he thinks the company that he works for stinks or something like that.

15:25
So that’s not the type of vulnerability I think that is healthy for a company.

15:29
At the same time, vulnerability around just being a whole person and bringing your best whole self to work is something that that has worked for me and is super important.

15:38
What about, you know, sharing stories of, you know, failure or, you know, mistakes that you’ve made in the past, you know, that type of vulnerability to say, hey, look, I’ve had deals where I’ve screwed up, you know, and this is what I’ve learned from it.

15:54
These were my ’cause it is all about like, hey, everybody falls down, everybody fails.

15:58
But it’s about what I learned from that experience, right?

16:01
Absolutely.

16:02
I mean, I think about some of the times that I’ve interviewed for new positions and really what I’ve looked for in the people that I would be working work with both laterally and you know, people that would be, you know, up line for me, whether it be a CRO or ACEO is just a sense of I, I guess we do come back to that word vulnerability.

16:21
Because if ACEO or a CRO or a sales VP or whoever’s one level applying from you can be vulnerable to their humanity, that is massive.

16:31
Because like I, I wouldn’t, frankly, I wouldn’t go work for a company if I could at all avoid it where I felt like the, the person upline for me was in it for themselves.

16:43
Or, or, or or doesn’t have kind of that, I guess sense of ironic self-awareness that, that, that I value and hopefully exhibit being able to say, you know what?

16:55
It’s kind of solidarity, right?

16:56
We’re all in this together.

16:58
We all know work is work.

16:59
We all know every day is not going to be perfect.

17:01
We all know that there’s systems and processes that suck.

17:04
There’s going to be deals that you thought you had that you know, fell apart at the last minute.

17:09
And guess what?

17:10
It’s not always somebody’s fault.

17:12
Sometimes it just happens.

17:13
Sometimes it is somebody’s fault.

17:14
And so we inspect it and inquire and and none of this has anything to none of the thing, none of this in any way excuses again, bringing your best whole self to work.

17:25
That’s right.

17:26
And I, and for something like myself, who’s very demanding, there’s a Ying to that Yang, if you will, like I’m very demanding and have very high standards.

17:36
And that would be a little bit much if I didn’t also, I think bring the vulnerability and the oh, by the way, I suck sometimes too kind of idea.

17:45
I agree.

17:46
It’s to me, you know, it’s, it’s hard to get your team to really buy into that.

17:53
Hey, I’ve got your back.

17:54
I’m here to help you if you don’t have that level or at least some level of vulnerability, because they’re, they’re going to think like this guy’s full of it or this woman’s full of it, you know, like they, they’re, they’re talking out both sides of their mouth.

18:07
You know, we’re like, oh, I’ve got your back.

18:08
But then I’m a step on you if I need to, right?

18:12
And, and really what it comes down to when I look at it is how do I inspire my team to their best performance?

18:18
And so there’s, there’s this is oversimplifying and I don’t mean to create a false dichotomy, but if I create two ways of doing it, we’ve all been there before.

18:27
Most people listening to this, and certainly you, Chris and I have been in these trenches for decades, frankly, there’s the person who leads by fear and there’s the person who leads by positivity.

18:37
And now there’s, there’s shades of that.

18:39
It’s not black and white, but I’ve reported to enough people who lead by fear in my life to just know that that didn’t really work for me.

18:51
Because when you’re led by fear, what happens is is that it kills creativity.

18:56
It kills self initiative because you feel like every little thing you do, you’re not sure if it’s going to get slapped down and so you aren’t on your front foot and you lose your confidence and confidence going into a sales call is absolutely massive.

19:12
And knowing that you belong in that room and knowing that you’re bringing value and knowing that you that you’ve got, you know, people have your back behind you.

19:21
And so that negativity like management or management by fear, management by like, again, I’ve put people on on performance improvement plans, I’ve fired people.

19:32
So it’s not to say that it’s all sweetness and light, but I’d like to fire people and I don’t like to put people on performance improvement plans.

19:40
And so managing by the threat of that is really negative in, in my current business and in the last couple businesses that I’ve LED, I’ve avoided the word quota.

19:50
I use the word sales goal.

19:51
And really it’s the same thing, but I just think that there’s kind of a negative connotation to the word quota.

19:56
And so I don’t, I don’t use, I’ve excised the word quota from the terminology and the sales playbooks that I put together just because again, I want to create an environment and the culture of positivity and that’s all running through the wall together as opposed to, you know, ultra hierarchical command and control and management by fear.

20:16
Yeah, I so that’s the thing I think people may just or may not appreciate is that you can do everything you’re talking about and still have accountability at the same level you would if you’re fear based.

20:28
But it’s a totally different environment.

20:30
It’s a totally different paradigm in terms of leadership because you’re saying like you’re saying, I think what’s really important is that you’re giving people freedom to move and do what they think is right.

20:41
You know, you’re not just locking them into this narrow path because there’s no way you can, you can’t control everything.

20:50
You have to trust your otherwise why do you have a team and you got to let them use their brains, right?

20:55
Right.

20:55
I mean, I think the analogy would be to sports.

20:58
I mean, somebody who knows that they is, is on the field, whether it’s soccer or football or whatever, they know that they belong there.

21:06
They know they can perform because they’ve performed before.

21:09
They know their coach has their back.

21:11
That’s the athlete who’s going to be able to have the creativity to get that three pointer from the arc or from, you know, from what they call the logo.

21:18
That’s, that’s all, all the rich right now with Caitlin and, and all that stuff.

21:24
But yeah, so the creativity that that you have the ability to to produce and the confidence you’re able to have when you feel safe.

21:33
And, and, and by the way, you know, my wife works in what’s called organizational development.

21:37
She’s got her master’s in positive and organizational development.

21:40
So you can imagine how fun our conversations are at the table.

21:44
The kids kind of go off and play their video games or go do their homework.

21:46
And we just keep talking about like, what’s a positive work culture look like?

21:50
And she led me to an article from the Harvard Business Review some years ago on psychological safety, which is a phrase I’ve never heard before.

21:58
It’s not a phrase you hear much in sales.

22:00
Frankly.

22:01
No, I’ve never heard it before.

22:03
And the concept of psychological, and again, you know, because it’s in the Harbor Business Review, it must be true and real, right?

22:08
That’s right.

22:10
But no, it’s a great article and the concept of it is really what I’ve been talking about without naming it.

22:15
But the idea is that if you get your best whole self to work and know that people have your back, it doesn’t.

22:23
It doesn’t preclude a culture of high performance and accountability because especially in sales, anybody listening to this knows the numbers don’t lie.

22:31
But how do you get to those numbers?

22:33
Do you get to those numbers through feeling like you’re scared and afraid that you’re going to lose your job?

22:37
Or do you actually get to the numbers better by feeling good about your work, looking forward to coming to work, coming to the work with a sense of positivity and collaboration with your team?

22:47
And of course, you’re trying to be the number one on the stack ranking.

22:50
But being #1 or #2 on the stack ranking, when you care about your teammates and you can pop your hand up and ask questions and get help from your manager, get help from a colleague, everybody working together in that world.

23:01
If you’re in a sales kind of, you know, kind of a like a team environment or even if you’re working remotely, just, you know, ping somebody on your messaging system to be able to get some help and not kind of be that lone wolf.

23:14
So psychological safety in sales is something that I’m super, super interested in because it’s not a concept that gets talked about a lot.

23:22
But I believe that you can have that, which sounds like a very soft factor.

23:27
You can have that in service of the hard factor, which is very high performance.

23:33
And frankly, when I think about all the times that I’ve been happiest and most productive as a sales Rep, back when I carried the bag, that was when I felt like my my manager had my back.

23:44
It felt like I knew what I was doing and that I kind of just had the wind at my back.

23:48
And I was just, you know, just, you know, flying along.

23:52
And that’s all that psychological safety does is it gives you that sense of we’re in this together.

23:57
People have my back.

24:00
I’ve I’ve been given the tools that I need to, to succeed.

24:03
In other words, whether it be playbooks or one sheets or, or, you know, battle cards or whatever it is.

24:08
And I’ve been trained properly to be able to add value to those conversations.

24:12
That’s the that’s the healthy recipe to repeatable sales success outside of just getting lucky with like a product that’s just, you know, flying off the shelves or, or, you know, everybody having to be like the best salesperson since Tony Robbins or whatever.

24:30
So, you know, scaling it up and having multiple people be able to have successful times.

24:35
You have to create that culture to enable that to happen.

24:37
Yeah.

24:39
You know, as you were talking, I was thinking of, you know, I, I took parenting classes, you know, two, I have two kids and parenting classes that like, you know, a lot of people do.

24:48
And one of my key takeaways are I think is very parallel to what you’re saying is that you could be that parent who is completely free will and do whatever the heck you want, no boundaries.

24:58
And the kids founder, you know that typically they just, they found her because they don’t know where to go or, you know, there’s, they have absolutely no direction.

25:07
Then you have the other extreme where their parent is trying to control absolutely everything that kid does and you have a totally miserable child.

25:15
And then you’ve got, you know, what I learned was like, you just have to set very clear boundaries.

25:20
Kids want boundaries.

25:21
They don’t want to know where the limits are.

25:23
But beyond that, let them be kids go out and explore and fail.

25:28
Let them fall down.

25:29
We don’t have to wrap them in bubble wrap.

25:31
They’ve got to learn through failure, right?

25:33
And so that’s a very simple analogy, but I think it applies to, you know, like you got to set the direction, the goals, the limits, right?

25:42
And then go out and have a good time.

25:43
Go, you know, learn, achieve, right?

25:47
OK, So what I’m learning here is that I’m going to add to my many dating analogies that I use when I’m talking about sales, and I’m going to use parenting analogies when I talk about sales culture and sales management.

26:00
OK.

26:01
You can’t tell me you’ve never thought about how similar sales is to dating.

26:05
OK, It’s I tell you that’s that’s hilarious.

26:08
Yeah, I haven’t really.

26:10
I’ve been dated for many, many years, don’t get me wrong, but I, I, I have dated.

26:14
Yeah.

26:15
No, it is.

26:16
It’s like you got to make sure you’re a fit, especially when you’re building a team.

26:20
You’ve got them.

26:21
You’ve got to know what’s going to fit what kind of personalities and, and what kind of drive.

26:28
So when you’re recruiting a team, how do you leverage this, this paradigm you have around psychological safety as part of your recruitment strategy?

26:40
That’s a really good question too.

26:41
I, I, I think that I do fall back to some principles that I’ve learned in recruiting over the years.

26:48
And, and this is something I’m sure you’ve heard before, but it bears repeating.

26:53
I think is, you know, I go into any interview and by the way, similar to this, it’s just a freewheeling conversation.

26:59
Obviously I ask questions and I have goals and I, I almost treat it like jazz.

27:02
Like in jazz you’re in a key, but but then you kind of riff within the key as opposed to being super structured like classical music.

27:10
So my interviews and frankly, a lot of sales calls are like that, have been like that as well, where I know what I’m trying to get to and I know the basic structure, whether you’re using spin selling or solution selling or challenger or whatever.

27:22
I’ve learned all those backwards and forwards, you know, kind of the structure of a call, but if you know it so well, then you can kind of riff on it within the structure.

27:30
But interviewing’s the same way.

27:31
So with interviewing, I know that I want to get in that all I need to learn and it might be different questions that just kind of pop up that get me there.

27:39
Do they get it?

27:41
Do they want it?

27:42
And I even add, do they need it and do they have the capacity to do it?

27:48
Interesting, get it, want it capacity.

27:51
And you know, I’ve read my share of business books that comes from a business book called Traction, which a lot of people, my last company lived Traction like lived and breathed it.

28:04
And I, we had a lot of success with it.

28:07
And so even though my current company doesn’t use it, specifically amongst my leadership team, I’ve kind of brought some of those principles in and, and kind of taught some of that stuff to others as they start interviewing.

28:19
But you know, do they get it?

28:20
In other words, do they understand their role?

28:22
Do they understand their place?

28:23
Do they under will they relatively quickly be able to acclimate themselves into this role and be able to learn the subject matter to be able to then be that subject matter expert to be able to, to do it?

28:36
So, for example, I’m not a big high finance guy.

28:39
It would take me a long time to be able to really, really sell complex banking instruments and the banking as a service and all that kind of stuff.

28:49
I think like a lawyer.

28:50
So law stuff is, is more natural to me.

28:53
And there’s a difference between those two.

28:54
I’m not a numbers guy.

28:55
I’m more than ideas guy.

28:57
Do they want it or even need it?

28:59
I’ve, I’ve made mistakes in the past where I’ve really including fairly recently where I, I only went with the want it and I, and I didn’t really go to need it.

29:12
And what’s need it mean need it doesn’t necessarily mean that if they don’t get this job, they’re going to be destitute, but need it means often times in sales, it means are they hungry for something income or advancement or something that will, that will motivate them and, and, and cause them to go the extra mile.

29:36
And it usually in sales, frankly, often is financial goals.

29:39
It could be short term midterm or long term financial goals, but that need it needs to be there as a or want it, need it.

29:46
Have you rephrase.

29:47
It has to be there as a career thing that is like, you know what, I cannot fail and I will not quit For these reasons.

29:56
And so a hire that I’ve done fairly recently, I think that person wanted it somewhat, but I maybe over emphasized how much they wanted it and ended up finding out that the person really didn’t need it.

30:13
And, and, you know, leave it at that.

30:16
And the capacity, capacity is kind of similar to get it, but capacity means, you know, do they, I get, I do sometimes kind of mistake, you know, the difference between get it and capacity to do it.

30:29
They’re similar enough, but, you know, they’re another way to look at, you know, do they have the what it takes to be able to succeed.

30:38
Those are the things that I look for in interview.

30:40
Yeah, that’s interesting.

30:41
Let’s shift the conversation just a bit here.

30:43
CRM, do you love it or do you hate it?

30:47
Do I get it?

30:48
Do I want it?

30:48
Do I have capacity to use it?

30:50
Yeah, we’re going to talk about that.

30:52
I’m totally going to tie that in.

30:54
I’ve been using CRM like most people have, you know, basically my whole career.

31:01
Of course it’s important.

31:03
There’s good roll outs and there’s bad roll outs.

31:06
There’s and bad roll outs don’t have to stay bad roll outs.

31:09
They can be fixed and sometimes for a lot of money, if you set the bone wrong the first time, you sometimes have to re break the bone and then reset it.

31:19
So there’s an analogy for you.

31:22
But no, I mean CRM, you know, I know you talk a lot about CRM in in all aspects of your life.

31:28
You’ve heard the phrase single source of truth.

31:30
I mean, you know, if you can get your finance data, your customer data, your, you know, sales data about like how many units of this or that or the other.

31:40
If you can get that all in there and then be able to do some even simple reporting and have those reports be standardized and scheduled week by week, you’re ahead of probably 70% of the world.

31:51
I’ve been there.

31:52
I know what good CRM looks like and good frankly, revenue OPS or sales OPS that helps get it to that place.

32:00
I’ve also been places where the data is, shall we say, more elusive.

32:07
So, you know, I’m a big believer in that.

32:10
You know, I, I look at CRM from the perspective of a manager.

32:13
If I’m a user of CRM day-to-day in my deals, yeah, you know, I get the muscle memory I need to be able to find out what to click when and what and what I’m supposed to do.

32:22
And so we roll out specific kind of practices or rules on how to populate the right fields in the CRM to make sure that we have what we need to be able to kick some reports out.

32:33
You know, that’s a, that’s a, a basic outline.

32:37
Now I would like to be able to, and I’m sure there’s tools out there to do it.

32:42
I’m not going to say my current company is to the place where we’re at this level of, of sophistication, but I would like to be able to not just use CRM data to report on the past, but you know, you start getting into like BI and analytics to be able to kind of have those past insights be able to predict the future or predict, you know, you know, A or AB or AC type of type of, you know, if we do this, this is what the outcome is and we kind of believe that that’s what it’s going to be.

33:09
If we try B, we’ll get these kinds of outcomes.

33:12
That’s the next level stuff.

33:14
I hope to get there with my current company in the next year or two.

33:17
So that’s awesome.

33:18
That’s awesome.

33:20
So when you look at your current CRM implementation, if you had a magic wand that you could wave to fix one thing and make it better, what would it be?

33:33
Currently we have and without using any names currently we have a bit of a disconnect between what you might call like Martech and, and, and sales tech.

33:47
Oh, again, I’m not going to use any brand names, but we’ve got some things that we use to help us get marketing emails out.

33:55
And, and like a lot of companies our size, we’re not tiny, we’re not a start up, but we’re also not Oracle.

34:01
We’re somewhere in between about 450 people, but with multiple instances of CRM.

34:06
Even with that 450 people because we’ve got these discrete business units that really do run pretty independently.

34:11
So we’ve got a instance of of our CRM for my, the business that I help lead.

34:19
And even in that third of the company that I help lead, we have 5 products where there should probably be two.

34:30
And a lot of that comes, a lot of that comes from the fact that we use third parties.

34:34
A lot of companies our size and smaller use third parties for scalability on on marketing operations or on, you know helping get things out the door because we run lean.

34:45
You know, companies ourselves tend to run lean in marketing sort of 10 people that are content marketers and copywriters and all that kind of stuff.

34:53
We’re very lean and so we rely on quick scale up and scale down using third party agencies.

34:59
Well, again, without using names, one of our third party agencies wanted to use product X and so they’re using product X kind of off in a silo.

35:07
I’m trying to, we’re trying to figure out how to get that data into our CRM through product Y, which is our standard Martech product.

35:16
That’s So you asked the question.

35:17
It’s kind of an ugly answer, but it’s kind of a hairball scenario all over again that we’re working on.

35:22
It probably surprised people when you when you gave your answer, I said, oh, good reason I said, oh, good.

35:26
Is that’s a real meaty topic that a lot of companies are struggling with.

35:30
That’s very common.

35:31
I see that so much and it’s happens exactly how you described.

35:36
It’s like, hey, we’re, we’re starting out, we’re growing.

35:39
This is the budget that we have available.

35:41
What can we get to do the job?

35:44
Yeah.

35:44
And while it may work for a little while, eventually it’s going to hit a wall.

35:50
And you could, you know, how do I deal with that?

35:53
And it’s, I think one thing that people have to understand is like anything else, you know, your, your, your technology infrastructure for sales and marketing has to grow with the firm.

36:07
And so I get asked a lot like, hey, Chris, what’s the right CRM for our business?

36:12
And basically what I tell them is don’t buy ACRM for the way your business is now.

36:17
Buy it for where you want your business to be three to five years from now, which is hard to envision.

36:23
But everyone, you’ve got strategic goals, you’ve got a plan where you want to be in three years or five years.

36:29
That’s what you need to be buying for.

36:31
Because that platform should, if it’s done right, if it’s implemented correctly, it will help you get there.

36:37
And so when you get there, you obviously want a platform that’s going to continue to support, you know, the next set of strategic goals and, and where that stake is going to move.

36:48
No, nobody’s stopping, right?

36:50
We’re all trying to grow all the time.

36:53
And so that’s when you get into that position where now, hey, we’ve got all these silos.

37:01
It gets expensive, it gets hard and there’s no easy answer to that.

37:06
But it’s something that like anything else, you have to have a strategy for, you know that then it has to align with the business, right.

37:14
And I guess the only thing I would really add to that too, is that it, it, it’s necessary.

37:19
We talked about single source of truth, but at the same time, it is necessary to have tools that play nicely with others.

37:26
Well, of, of the capabilities to bring like ABM technology into CRM to be able to be a smart overlay so that you kind of know who to go after based on some ABM, you know, whether it’s, you know, internal IP addresses or cookies or whatever.

37:42
To be able to kind of determine who’s closer to market, who’s who passes like a warmth score, even if they’re not raising their hand.

37:48
That’s, that’s a constant thing in our world is how do you get to the people with the right messaging at the right time if they’re not raising their hand?

37:56
Because if they raise their hand, it’s easy to score that a certain way on X system to be able to score it to say, OK, that’s going to be a lead or an MQL or whatever it is.

38:04
I’m a big believer in the fact that the data is out there.

38:09
And in my business, my I go again, we’re back to the bankruptcy business.

38:14
We kind of know who all the bankruptcy lawyers are.

38:16
Like, you know, we don’t need to go buy lists or something like that.

38:19
Like, you know, there’s a lot of list sellers.

38:21
It’s a defined universe, right?

38:23
We know who our bankruptcy lawyers are and we’re the biggest player in in that space.

38:26
And so we have 10,000 of the 14,000 on our platform in some way, shape or form, there’s maybe 15,000 people that matter to us.

38:34
And we know basically who those 15,000 people are.

38:37
But what if we could use the e-mail addresses that we have and this is kind of lower level ABM, but be able to kind of say, OK, follow them around the Internet and get them ads on YouTube.

38:47
I’m kind of getting more marketing side stuff, which is something that I’ve grown into, frankly.

38:51
You’ll find that sales leaders as they advance in their career, they realize that it’s all one big revenue puzzle.

38:58
Yeah, it really is.

38:59
And and that’s not that’s not new news to you.

39:01
I’m sure anyone here in my previous episode for sales, Lee, Doug, we were talking about that, that that unification between sales and marketing, that they can’t be separate entities anymore where you’re just throwing stuff back and forth across the wall.

39:16
They have to work as a unified team to be effective these days.

39:20
It’s just it’s too complicated too or there’s the competition levels just gets higher and higher every year, right.

39:26
And I you need to be able to react quickly.

39:28
Yeah.

39:29
And I would say that in, in, in businesses that are focused on mass outreach to lots of entities for smaller transactions, which is our business is even more so than the enterprise whale chasing entities.

39:46
Now don’t get me wrong, marketing is just as important, but in a different way for for organisms and I’ve worked for both types.

39:52
Currently I get I’m in a position where it’s really kind of a mass marketing operation with targeted smart sales effort at the highest value interactions.

40:03
That’s a.

40:04
This is not a a playbook that I’m so unique to make, but if you’re going to use human resource towards the sales problem, you’re going to put that human resource towards towards the the highest value opportunity because that’s not as scalable as getting digital and e-mail marketing, right.

40:22
So, yeah, so coming back to the martech discussion, you need a platform.

40:28
Yeah, I talked about unifying sales and marketing.

40:30
Your technology should be unified as well.

40:33
That doesn’t mean, and this has to be the same platform.

40:35
That would be the ideal solution.

40:36
And there are vendors out there that have those capabilities.

40:41
But if you don’t have that platform, then you better have a really good integration strategy so that they act unified.

40:49
I think that’s the key.

40:50
Yeah.

40:51
And I, I, you know, I don’t, I am not the CRO, I’m the VP of sales.

40:56
And so I work closely with our marketing people and you know, I kinda own sales, the, the, the, the, a part of it on the sales side.

41:07
And, and then marketing kind of owns another part of it that is kind of that automation stuff.

41:12
Of course the automation stuff goes into the, into the, the CRM.

41:17
And so the, the issues that we sometimes run into are that we aren’t able to sometimes get the data to sometimes even match up sometimes that they will come across.

41:32
And, and so again, you know, our instance of our, of our CRM is not anywhere close to where it needs to be, but we’re working on that right now to get it cleaned up kind of that broken bone concept.

41:42
But yeah, being able to, you know, if we say give me all lawyers who have bought this many units of this between this.

41:50
And this.

41:51
Like that’s pretty XS and OS, that’s pretty black and white.

41:55
And if one system gives you one number and another system gives you something radically different, that’s the kind of stuff that, you know, Frank, got a problem.

42:02
You got to agree on that on that on on a number.

42:05
Otherwise, frankly, and the last thing that you want, I mean, this, maybe this is a message for other sales leaders is you better get along with your marketing leaders and and you better agree on numbers because relationships and teams go down when you aren’t on the same page and we don’t agree on numbers.

42:22
I think we’re going to end this episode of Sales lead dog right there.

42:24
There’s a good spot to end it.

42:26
Jason, really appreciate you coming on the show.

42:29
If people want to reach out, connect with you, if they want to learn more about Stredo, what’s the best way for them to do that?

42:36
Sure, they can find me on linkedinimlinkedin.com/IN/jason D Grimes.

42:42
So I was able to personalize that.

42:44
So yeah, that’s an easy one to find that.

42:46
That’s my LinkedIn that’s easy to find.

42:48
Feel free to reach out and connect on LinkedIn.

42:50
I I will say that I’m a big believer in knowing the people that I connect with.

42:55
I’ve got over 1900 connections.

42:58
I’ve met every single one of those people.

43:00
No kidding.

43:01
Sometimes it’s on a Zoom, but I’m not an open networker.

43:04
But if you reach out to me, maybe we have a networking call.

43:06
And I’ve had so many meaningful networking calls with people in our industry and others through through that type of interaction.

43:13
So I would value A5 or 10 minute call and then we can get and see how we can help each other.

43:17
That’s awesome.

43:18
That’s awesome.

43:18
So if you didn’t get to that URL, that’s OK.

43:20
Get it in our show notes.

43:22
You can get the show notes at Impeller CRM com/ sales Lead Dog where you’ll find not only this episode, but all the 100 plus episodes of Sales Lead Dog.

43:32
Be sure to check that out.

43:33
Be sure to subscribe so you get all our future episodes.

43:36
Jason, thanks again for coming on Sales Lead Dog and welcome to the Sales Lead Dog pack.

43:41
I love it.

43:42
Thanks, Chris.

43:42
Appreciate it as we end this discussion on Sales Lead Dog.

43:49
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43:54
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43:57
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44:07
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Quotes:

“Unlocking the secrets to a high-performing sales team starts with a culture that embraces vulnerability and authenticity.”  

“The leap from insurance to legal tech sales wasn’t just a career shift; it was an integration of my legal expertise into a winning sales strategy.”

“The internal sale is just as crucial as the external one. Gaining stakeholder buy-in at all levels is key to a thriving sales environment.”  

Links: 

Jason’s LinkedIn  

Stretto Website  

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