How do you retain good talent, especially when sales roles are in such high demand across the industry?

Another topic that is always top of mind for sales leaders, and their recruiting teams, is their employee retention scores. It is a massive expense to organizations when they see talent leave, whether regrettable or not, and have to spend resources recruiting, enabling and eventually filling that seat. Programs, behaviours and approaches that may help keep your teams intact and excited about their role, can include:

- providing new challenges and opportunities. This can come in many forms of internal career growth avenues, including progression through the sales segments, offering leadership opportunities, and/or programs and resources made available for personal development.

- Engaging with your employees on a regular basis. Demonstrate to your teams that their feedback is welcomed, valued and encouraged. You've seen this done with internal 'employee engagement' surveys, 'ask me anything' panels with leadership, and of course it all started back in my early days with the physical 'suggestion box' (dating myself slightly).

- Expand your 1:1's to be more than just about deals and quota. There is more to a seller than their ability to sell. Think of what 'behaviors' you want your team to excel at..are they good collaborators with cross functional teams? Are they a good team member and help mentor new members and don't shy away from sharing learnings? Do they show up prepared, educated, and lead with the customer first? Also, think of what sales 'competencies' you want to ensure the team excels at, such as being strong at doing 'discovery', they have the ability to tell compelling customer stories, and are they doing account plans for their tier 1 accounts?. If you build a team with strong sales 'behaviors' and 'competencies', the quota retirement will come.

- Celebrate and acknowledge. Celebrate both big and small things within the sales org, and set up a recognition program outside of your 'Presidents Club' (or equivalent). Everyone responds well to their positive acknowledgment and reinforcement.

Without sales, you don't have a business. Talented sales people are hard to find and even harder to retain. Here are a few questions I ask: Are your sales people bought in on the company mission and the future of what your company is building? Do you recognize them for their hard work and contributions to the company? Are you providing competitive compensation for your sales people? Do they believe they're working under the best sales leadership team that will continue to foster a positive and supportive sales culture? Is there a clear path to promotions that offer growth opportunities? Are you regularly offering feedback, sales coaching and support?

While tech may have downsized lately, great sales professionals still have lots of options. The major driver of recent layoffs were to create more efficiencies in businesses; which leads to lower burn and more profitability. There are few roles as efficient and impactful on profitability as a top seller exceeding their quota. By nature these folks will always be sought after and have options - so retaining top talent should always be a priority.

The biggest mistake I see in retaining talent, is front-line managers DAM'ing their team. They only manage:

D- Deals - when the deals are there and closing life is good! When they're not, the only lever they have is to drive activity.

A - Activity - when deals are there, activity check-in's are infrequent and leading indicators of poor future pipe are missed. Once the pipe dries up, poor managers micro-manage activity and ramp up the urgency on activity without offering much actual guidance on how to drive better conversions. "Do more" is the mantra.

M - Morale - any decent manager is going to check-in with their team. If they aren't truly helping their AE be successful then morale will probably be good when they're winning, and lower when they're not. Especially low when they're being micro-managed for prospecting...

Now let's compare this and understand why a top performer would stay in the first place. There are 4 core reasons and an elusive and fleeting 5th reason.

1. They feel successful, are making money, and feel they're being fairly rewarded for their work.

2. They're developing skills and growing. They know that the hard work they put in today will pay dividends down the road.

3. They see opportunities for career progression and advancement. They believe there is opportunity to get promoted, or take on meaningful work that would represent professional growth, in an acceptable timeframe.

4. They're having fun and/or enjoy the people they work with & for.

If you hit all 4 of these and/or if you are a part of a very mission-driven organization with inspirational leadership, you can tap into the 5th category:

5. They feel like they're a part of something bigger than themselves.

This last one is a by-product of doing a lot of other things right. But if you can reach that pinnacle - this issue will take care of itself.

Now if we apply the DAM method to why people would stay:

1. If the deals are there, the DAM Manager would theoretically focus on and help the AE close their deals. When pipeline is present the DAM method can work. Of course if it's not - this is strike 1.

2. Outside of situational deal coaching, there's no skills development carved out in the DAM method

3. Promotions are a by-product of hitting your number or not

4. It's fun when you're winning and unless you're on a great team, you don't really enjoy where you work when you're in a slump.

A normal person needs 3-4 to feel good about where they work, 2 to be okay with it, and 1 to begrudgingly stick around. Literally everything above is dependent on there being enough pipeline and the AE closing deals. There is absolutely no reason for someone to push through to the other side when things get difficult. This is what causes someone to hit the bare minimum of requirements and demand a raise or promotion. They aren't having fun (4), they're not developing skills (2), they aren't making the money they want to make (1), so the only way to justify their existence is to get promoted (3) - which will give them fleeting relief until they move on 6 months later after the other 3 don't change and the next promo is 2 years down the road.

So what DO you do:

1. Everything is easier when you're winning. I'm not going to break this down too deep - but more people feeling successful, hitting quota, making money, setting records, the more they'll want to stick around and keep doing it. Also check quotas to ensure they're realistic, attainable and surpassable. Make sure comp is competitive and I'm a big fan of accelerators to ensure your most talented AE's put the hammer down after they've hit quota instead of backing off. You can also get creative and make the highs higher. President's Club produces so many memories and is a silent motivator throughout the year. Hi-Po dinners or events for top performers throughout the year are another worthy investment. Once you've had a taste of being in the exclusive club for top performers you never want to back.

2. Working on Skills Development is where I think most companies can improve their standing with talent. Learning slowed down when we went remote. You used to have to be less intentional, and the osmosis of hearing everyone do the job, or being able to ask your neighbor a question, improved skills naturally. This has dropped off a cliff. According to the Bridge Group, ramp time now sits at 5.7 months compared to 4.3 months in 2020. This is an industry wide problem. While you can (and should) analyze your onboarding program, possibly hire outside training for a shot of adrenaline, and look at your enablement team for help here - it's not all on enablement. The gap is more on day to day coaching. Leaning in and investing in your front line leaders to be better coaches and develop THEIR skills to uplevel the AE's skills is where you'll have the biggest impact in my opinion. The bar for this also gets higher as the AE gets more talented, so it's important that front line leaders can not just coach the basics, but can help talent get to the next level. "Coaching" or "skills development" in general however just doesn't take up much real estate on enough managers' calendars.

3. Upward mobility is another silent motivator that drives people to keep working hard in the background. If your most talented people have reached the highest rung - you should identify this as a risk and think through if there are opportunities to create a new promotion level, carve out more responsibility, or add a rung to the ladder in some way. I've interviewed so many AE's who were talking to me because they felt "they had learned everything they can at their current company." Don't ever let that be the case, or don't be surprised when they leave. One thing I undervalued coming up as a leader was clarity of promotion path. I thought it was obvious that if you performed at an elite level, you would be in the conversation for a promotion. Some people can put their head down and operate at their best under these guidelines, but you miss your core performers. Core performers hate this answer, and by getting more clarity around the exact expectations for a promotion, you can often get more out of these folks as they work towards checking off all the boxes. I have also tried to talk talented people off a ledge who felt like it just wasn't clear how they get to the next level. We need to know that taking a new job, with a new title, at a new salary, is always crystal clear. So if someone is in their office at home, thinking through their next couple of years - if they can't see how they would move up in your organization, it's going to be a lot easaier to believe their easiest path is to go somewhere else. Change this, and prove it. It's so important to show promotions and ensure everyone knows those stories - what they did, how they did it, and how "you too can get those same results."

4. In a remote world "fun" is a lot harder to come by. I used to love coming to the office. My teams typically loved it too. We had a great group of people that genuinely enjoyed working together for the most part. Energy was through the roof. We had tunes going, people on the phone, we celebrated everything, gongs were ringing, jokes were made on the floor, deals were broken out live, people were learning, succeeding and had camaraderie around them to push through it if they weren't. We'd go out together from time to time and we made work fun. That is just near impossible to replicate in a remote world (if you have the secret sauce DM me!). What you can focus on however is building culture. Putting together an intentional team that wants to lean in, engage, and work together in this new capacity. Create opportunities to collaborate, learn and grow together. Anoint members of your team who have a pulse on the rest of the team to step up and help drive this so it lands. They can fill your blindspots. Invest in getting people in office whenever you can. If someone really likes their boss, this can make a huge difference too. Ensure your front line leaders are a big plus in this column. Which leads us to number 5

5. While a lot of things need to click for the team to feel like they're a "part of something bigger than themselves" there's one quality that will keep people around well beyond the point of logic, and help create a dedicated army for the cause. Inspirational leadership. You can find this at all levels - however you've heard about an inspirational leader behind many of the world's most iconic runs. Tesla had Elon Musk. Apple had Steve Jobs. Yammer had David Sachs. Hubspot had Brian Halligan. OpenAI was about to lose the whole company when they tried to oust Sam Altman. People will follow inspirational leadership through hell and come out the otherside unscathed and still committed. It doesn't need to be a silicon valley legend however. There are inspirational managers, directors, VP's and team leads across the industry. I feel this is undervalued however. If talent is really thinking about leaving - are they inspired? Are you inspiring them? If this feels like a gap - start with clarity of the Mission. What hill are we taking, what's our goal - beyond just hitting revenue targets. What's the strategy for hitting that goal? Why does that matter for the team? What's in it for them? Why are they lucky, one of the chosen few, to be on that mission here and now? If you can answer all of those things - people are probably inspired. If not - it mght be a good exercise.

I map all of this out in detail to provide the ability to audit your own org, or an individual. You would love to answer yes to all 5, but identifying where the no's are can give you a clear roadmap on what to fix to systematically retain talent.

1. Do they feel successful, are making money, and feel they're being fairly rewarded for their work?

2. Are they developing skills and growing? Do they know that the hard work they put in today will pay dividends down the road?

3. Do they see opportunities for career progression and advancement? Do they believe there is opportunity to get promoted, or take on meaningful work that would represent professional growth, in an acceptable timeframe?

4. Are they having fun and/or enjoy the people they work with & for?

5. Do they feel they're a part of something greater than themselves?

Retaining top sales talent is crucial, especially in an industry where skilled sales professionals are in high demand. Here are strategies to help retain great talent:

1. Offer Competitive Compensation & Incentives

• Base Salary + Attractive Commission Structure: Ensure your compensation package is competitive, with both a solid base salary and a lucrative commission structure. High performers should feel their efforts are rewarded.

• Performance-Based Bonuses: Add bonuses for exceeding targets, closing large deals, or maintaining high customer satisfaction, which can motivate your team to stay engaged.

• Non-Financial Perks: Benefits such as healthcare, retirement plans, stock options, and flexible working arrangements can enhance job satisfaction.

2. Provide Clear Career Growth Paths

• Personalized Development Plans: Outline a clear career trajectory with opportunities for promotion, leadership roles, or specialization. Show top performers how they can grow within the company (e.g., from Sales Rep to Sales Manager to VP of Sales).

• Mentorship & Coaching: Pair high performers with mentors within the organization to help them develop new skills and prepare for leadership positions.

3. Invest in Training & Development

• Continuous Learning Opportunities: Offer training programs that help your salespeople improve their skills, whether in sales techniques, leadership, or industry knowledge. This can be in the form of workshops, certifications, or online courses.

• Upskilling on Sales Tech & Tools: Ensure your team is well-versed in the latest sales tools (e.g., CRM, AI-powered platforms like Freshworks CRM) to streamline their work and keep them ahead of the curve.

4. Foster a Positive and Collaborative Culture

• Create a Supportive Environment: Sales can be stressful, so fostering a positive, collaborative work culture helps. Encourage teamwork, celebrate wins (big or small), and offer support during setbacks.

• Open Communication: Create an environment where feedback is valued, both from leadership and peers. Transparent communication builds trust and helps salespeople feel heard and supported.

5. Recognize and Reward Success

• Recognition Programs: Regularly acknowledge and celebrate high performers publicly, whether it’s through “Salesperson of the Month” awards, team shout-outs, or internal newsletters.

• Non-Monetary Recognition: Consider non-monetary rewards like paid time off, travel incentives, or personalized experiences for top achievers.

• Tailored Recognition: Understand what motivates individual team members (some may prefer public recognition, others a quiet thank you), and tailor your recognition methods accordingly.

6. Offer Work-Life Balance & Flexibility

• Remote Work Flexibility: Many sales professionals appreciate the flexibility of remote or hybrid work environments. Offer options for remote work, flexible hours, and the ability to manage their schedule.

• Time Off and Mental Health Support: Encourage taking breaks, vacations, and mental health days to avoid burnout, especially in high-pressure sales roles.

7. Create a Healthy, Competitive Environment

• Foster Friendly Competition: Use leaderboards, sales contests, and incentives to create a fun, competitive atmosphere that drives performance without becoming toxic.

• Balance Competition with Collaboration: While competition can motivate, collaboration leads to long-term success. Encourage team-based goals and sharing of best practices.

8. Provide Autonomy and Ownership

• Empower Decision-Making: Give salespeople ownership over their deals and the freedom to manage their accounts. Empower them to make decisions and take the lead on key accounts.

• Goal-Setting Autonomy: Allow reps to have input in setting their targets or deciding how they achieve their goals. This autonomy fosters a sense of ownership and investment in their work.

9. Ensure Strong Leadership & Support

• Inspirational Leadership: Salespeople want to work for leaders they respect and who inspire them. Make sure your leadership is setting the tone with a vision and offering support to help reps succeed.

• Regular Check-Ins: Managers should schedule one-on-one meetings to discuss personal goals, performance, and areas for improvement, ensuring salespeople feel valued and supported.

10. Align Sales Roles with Purpose

• Connect the Role to Company Mission: Sales reps who feel connected to the company’s mission and purpose are more likely to stay. Help your team see how their contributions impact the company and its customers.

• Customer-Centric Focus: Encourage sales reps to focus on solving customer problems and creating value, not just hitting targets. This creates a sense of purpose and fulfillment in their role.

11. Exit Interviews and Continuous Feedback

• Conduct Exit Interviews: For those leaving, gather feedback on why they’re leaving and use this data to improve retention strategies.

• Regular Surveys: Conduct anonymous surveys to gather ongoing feedback from the sales team on job satisfaction, challenges, and areas for improvement.

Conclusion:

To retain top sales talent, focus on a combination of competitive compensation, clear career development opportunities, and a positive work culture. By investing in their growth, recognising achievements, and providing flexibility, you’ll build a loyal, high-performing sales team that is less likely to jump ship in a competitive market