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Jordan Rackie has crafted a career in sales that many sales reps would dream of – he started as a junior sales rep, before steadily rising up the ranks as a Senior Sales Executive and Sales Manager at Pardot, and now as the Director of Sales at PeopleMatter. He has become an expert in the field of SaaS sales, drawing from lessons from his mentors, as well as his own vast experience.

We recently had the pleasure to speak with Jordan on a variety of sales topics, including the importance of standardizing your sales process, the keys to effective sales pipeline management and the challenges of managing sales managers and sales reps.

1) What is the biggest difference between your previous position – sales manager at Pardot – and your current position as Director of Sales at PeopleMatter? Compare the experience of being a smaller fish in a big pond vs. being a big fish in a smaller pond.

I’m extremely excited to have input into the overall strategic sales process – putting in place strategies that allow for highly talented sales reps to rise to the top. At my last organization, it was very much put in place by my mentor – Derek Grant, the SVP of Sales at Pardot. He did a fantastic job of aligning processes that allow sales reps to be very self-sufficient and work within the model. In coming to PeopleMatter, one of the things that was attractive to me was that the sales process and standardization was still very much in the development stages.

2) You’ve had a pretty prototypical dream career for someone in sales, moving up linearly from sales rep to senior sales rep to sales manager and now, director of sales. What advice do you have for junior sales reps looking to rise through the ranks in a similar career path?

If you want to move within a sales organization, ask yourself, “Why?” Where do you want to be a few years from now, and why? Do you understand what it takes to get from point A to point C? Beyond that, just because you are a fantastic sales rep, doesn’t mean that you have to progress through management and/or that it’s the correct path for you. Michael Jordan was a fantastic player – Michael Jordan as an executive or manager? That’s still a little fuzzy.

Additionally, for junior sales reps, if you want to rise in the ranks of sales management, I would say go seek out help within your organization. At my previous stop, I shadowed my former boss very closely. The best mentors are happy to do so, but they don’t have time to continually ask people to shadow them and to learn from them. You have to be proactive and seek it out.

In conclusion, I’d recommend a junior sales rep who has career aspirations of moving up the proverbial sales leadership ladder to fully understand why they want to take that path. Proactively go out and shadow those you aspire to be like, and then ask yourself where you want to be 3-5 years from now.

3) It’s interesting that you had a background in basketball coaching – we recently ran a blog post comparing the similarities in coaching between sales and sports. What do you think are some similarities or differences?

I think a big similarity between coaching athletes and salespeople is that I’m working with very strong, type A personalities the majority of the time. Your team has to respect your work ethic, leadership style, and respect your knowledge and expertise. If you lose in any of those areas, the overall results will suffer.

Another similarity – it takes a team effort to get to the top. “As the tide rises, so do the ships.” You’re not going to win the championship and you’re not going to be the leader in the market unless it’s a collective effort by everybody. At PeopleMatter, we run daily standups and collaborate on the market daily, so that we are all up to date and have the best chance for success.

4) Earlier, you mentioned the importance of standardization in the sales process. Why is this so crucial?

Standardization allows for predictable revenue streams. It allows you to measure and recreate what works, while identifying and fixing what isn’t working. Without standardization, things aren’t measurable and scalable. For example, if an organization can identify at what age deals lose the likelihood of closing for the win, you can help coach your reps around the momentum thresholds necessary to give them the best chance for success, while eliminating those opportunities that are just a time waster or sunk cost.

5) Another critical part of the sales process is managing your pipeline. What do you think are some of the keys to effective sales pipeline management?

I think it’s important to analyze stage duration. Like I mentioned above, momentum and velocity are very important. If a trend is noticeable, there will be a need to audit the area for improvement and figure out what bottlenecks in your sales process can be fixed. For example, one way to track pipeline velocity is to develop a sales dashboard that allows you to see, on one screen, all the areas of your own personal opportunities. I recommend power ranking your reps in each bucket so that people can see how they compare to their peers – this breeds healthy competition.

Here is an example flow for an organization selling on a 30-60 day sales cycle: Open scheduled pre-pipeline meetings set (next 30 days) > pre-pipeline meetings held (last 30 days) > pipeline added (last 30 days) > in-pipeline meetings held (last 30 days) > open in-pipeline meetings (next 30 days) > opps less than 30 days old > opps greater than 31 days old. What you should be looking for here are trends in each stage. I actually like to start at the end and work my way backwards to a column that is producing less than stellar results. Those locations will allow for dissecting and coaching.

6) As a Director of Sales, you’re managing a lot of different types of people, including mid-management and junior sales reps. How is managing a team of executives and sales managers different from the more hands-on coaching of junior sales reps?

While it’s essential to remain consistent with the backbone of your coaching style, it’s equally as important to understand that no two reps are the same, and that adapting to the team you have is a requirement. Just as in sales you must adapt to your prospective client, a great leader can adapt to the team they have to get the most out of each person. More advanced, senior-type reps will need less generic sales training, and rather the focus should be on market and product training. The biggest challenge in attracting and retaining more senior talent is making sure you have the support structure and process down so that they can join the team and find success quickly. Many of the kinks in process should ideally be worked out before you bring them on, but once you get them to buy into the vision, it’s a great ride from there.

For junior reps, the challenge management faces is to make sure there is an ability to quickly identify great raw talent and potential, and coach and mentor appropriately. In a position where you have a large team of sales reps that have 3 or less years of SaaS experience, identify who takes a sponge-like quality and is able to absorb and reuse what is taught very quickly. You’re looking for a fast “chip speed” up top with a hunger and desire to be the best. When you find those people, they will require a little more time up front, but the return later will be exponential. You’ll end up with an earner who is also extremely loyal to the process and team that helped develop them.

7) One of the main concerns for senior sales executives is to forecast sales, for the month or quarter or year. What do you think the keys are to forecasting more accurately?

There are many ways to increase the accuracy of your sales forecasting. A sales rep must be able to confirm customer verifiable outcomes at each stage of the opportunity before they can move the Opp along to the next stage. If a rep can’t answer certain key questions and can’t confirm that the customer agrees that these key situations/questions have been addressed, then there is much more work to do.

Additionally, it’s very important to set the tone early that this relationship will be very transparent. The dynamics of any relationship are disproportionately shaped within the first minutes, if not seconds, of an encounter. We’ve all been taught that first impressions are everything. This couldn’t be any more relevant than within a sales cycle. Set the tone early, ask the tough questions immediately, address risk, price, and the competition off the bat and you will have established a relationship that facilitates the ability to forecast more accurately. You’ll get the data points you’ll need.

8) Speaking of forecasting, how do you foresee the sales industry to change over the next 5 years?

There will continually be a movement toward inside sales. When I first got out of school in 2008, I thought I was destined for outside B2B sales. Being face to face seemed like the only way to make it big. What I’ve found is that the internet tools that are out there today have allowed for the web to be a fantastic facilitator of efficient selling. That, combined with the fact that buyers are becoming more comfortable with initiating and continuing a B2B purchase completely web-based, makes me believe that inside/web-based sales is the direction things will continue to disproportionately head. In my experience, 6 years ago, buyers were comfortable with web transactions north of $10,000 ARR (annual recurring revenue). Now, I’m seeing web-based / inside deals happening that are north of $100,000 ARR. It’s a great time to be part of the wave!

More about Jordan Rackie

Jordan Rackie is the Director of Sales for PeopleMatter – an extremely fast growing SaaS organization that has over 3 million users, while only being in business since September 2009. Before that, he was an early and original sales leader at Pardot helping drive them to the $100 million dollar exit & ultimate acquisition by Salesforce.com.

A star sales coach, rain-maker, and leader, Jordan’s closed tens of millions in recurring SaaS revenue. 

Connect with Jordan on LinkedIn or Twitter

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