Beyond Baby Steps with Dave Ramsey and Suze Orman

The last 10 years have seen a major shift in sales force dynamics as millennials have entered the workforce in droves.  At Xamarin, I was an Old Guard sales leader with an organization full of millennials, and I had a ton of questions on how to lead the group. What motivates them?  How do you reward performance and how often?  How do you deal with conflict?  How should you handle good and not-so-good news?  How do you balance good attrition, bad attrition and Glassdoor ratings?  In Daniel Pink’s book Drive he puts forth a north star for motivating people that has been invaluable on this journey:  Autonomy, Mastery, Purpose.

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Some Things to Keep In Mind

1. Sales Skills and Development.

A Pod (e.g. SaaS sales team unit) can be downright unstoppable with the right combination of millennial and Old Guard team members.millenials

The Old Guard have a consultative (solution selling) skill set typically honed for selling high value solutions through long, complex sales cycles using things like MEDDIC.  While they are often excellent listeners, readers of people, and negotiators, they could rarely be described as lightning fast and they are not naturals online.   They tend to work best face to face with customers, they differentiate themselves with a deep knowledge of their customers and they establish long-standing relationships that intermingle their personal and professional lives.

Millennials do not have the same level of consultative selling skills as the Old Guard.  They learn to execute a solution selling process quickly but their execution, especially early on, is less refined and requires considerable coaching and support by sales managers before they can be truly autonomous.  On the flip side, they are incredibly pragmatic and share sales best practices with each other generously.  They are online and mobile natives who navigate customer research and social networks expertly, adopting new technologies to speed their performance near instantaneously.

2. Incentives and Drive.

The Old Guard of sales tend to be expensive, and motivated primarily by financial gain (e.g. big bonuses with accelerators).  Millennial sellers are also motivated by money (they are sellers after all) but their salaries tend to be lower because of their inexperience and smaller deal sizes.  Millennials also want a reward system that is effectively the gamification of career advancement.  As they perform and develop competency in their roles, they want recognition in the form of more senior titles, spot rewards and/or financial increases ~every 3-6 months.

Possibly the most significant difference is that millennials deeply desire their work be filled with purpose and aligned with their values.  Culture eats strategy for lunch every day, so your reward system needs to account for both financial and cultural benefits (lunch together daily, friendly competitions, positive tone/attitude, regular public praise, open floor plan, plenty of team outings, org-wide team building).

3. Recruiting and Employee Retention.

In no other employment segment is turnover higher than among millennials.  We all know that people leave managers, not companies.  The cost of boredom, managerial harshness, and unclear/long winding career paths can result in high turnover rates and poor Glassdoor ratings with your millennial hires.  Hire a terrific senior recruiter, and partner with local recruiting agencies (in the Bay Area Swing does great work filling sales and success roles!).  Go out of your way to connect with local universities by participating in job fairs and internship programs.  Get creative and have some fun — we hosted some killer recruiting parties at the office and found some terrific talent that way too!

4. Learning and Enablement.

Millennial learning and development is an ongoing ‘better every day’ affair while annual/semi-annual training is what the Old Guard is used to.  Millennials take interactive learning to a whole new level and have fewer inhibitions about learning/practicing/contributing in groups.  They are darn good students who want to learn and are fun to teach.  Learning gives life to millennials and is a big part of their value equation.

A couple of suggestions for onboarding millennials:

  1. Build your new hire onboarding experience to create ‘coachable autonomy’ for all your new hires before handing them over to managers
  2. Create a hands-on mentorship program so new hires can apply what they’re learning to real world settings in a relatively safe environment (increase difficulty level as you go)
  3. Measure new hire onramp progress in terms of results.  Track actual performance as a percent of their fully-ramped goals over time.  When new hires reach 100% of their fully ramped goal, celebrate them and give a small “congratulations” reward.  Then set the bar higher.
  4. Repeat steps 1-3 forever.

5. Old Guard Coachability

It would be unfair to say that you can’t teach an Old Guard new tricks, but let me say this.  The Old Guard can get stuck in old ways of doing things, and they can be downright cantankerous learners as it relates to sales.  SaaS sales organizations tend to be innovators and fast changers so when you hire Old Guard sellers, be sure to look for coachability.  The Old Guard tend to have a lot of experience so as a bonus, create opportunities for them to share what they know.

In organizations who serve both enterprise and prosumer customer segments, it’s important to get your mix of millennials and Old Guard just right.  These groups have a lot to learn from each other.  A good mix of skills and personalities can do wonders for your sales culture and effectiveness!

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About SalesSmyth

We created SalesSmyth because we knew there had to be a better way for growth stage companies to build their sales organizations.  We’re sales leaders and consultants, so we’ve seen firsthand the effects of building a sales team by the seat of your pants: higher burn rates, lower valuations, and less control over the future of your company.  So we ask ourselves the question that drives us, “What can we do to help entrepreneurs build high performing sales teams that lead to explosive growth?”  We are on a mission to deliver torrents of revenue by designing, training and equipping sales organizations to do their very best work.

About The Author

Sam Henry is an entrepreneur and sales executive who gets fired up about bringing new businesses and world-changing software to market.  Sam is Managing Partner at SalesSmyth a management consulting firm who helps design, train and equip SaaS sales organizations.  Most recently, Sam was Vice President of Sales Strategy and Enablement for Xamarin (acquired by Microsoft) helping to bring world-class mobile solutions to developers in businesses everywhere.  In 2009, Sam co-founded Henry & Company, an angel investment firm that invests predominantly in professional services businesses and Colorado real estate providing capital and hands-on engagement to drive growth.  Prior to Xamarin, Sam spent fourteen years in various sales and marketing leadership roles at Microsoft. Sam lives in the mountains of Colorado with his dream girl and their four amazing kids.

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