How can you develop your sales enablement career? Alicia Anderson reveals all

Sales Enablement Collective’s Slack channel played host to yet another awesome “Ask Me Anything” (AMA) session with Alicia Anderson, who’s been both Director of Revenue Operations and Enablement and Senior Manager of Sales Enablement at Convoy Inc.

Across her career, she’s led high-performance teams to exceptional results, collaborated as a trusted partner with C-level leadership, planned SKO programming, managed a customer advisory board program, oversaw the sales enablement tech stack, and facilitated new hire onboarding for sales.

Amidst her busy schedule, Alicia took some time to discuss navigating and paving your sales enablement career path with our community members. She touched on:

Missed Alicia’s AMA session? Don’t worry, we’ve condensed all her answers right here. 👇

But if you want to catch the next session live, and even ask some questions of your own, join our Slack community and keep an eye on our #announcements channel!

Standing out on your résumé and during interviews

Q: “I'm currently searching for my next challenge. What do you look for in a resume? What can someone do to stand out”

A: Oftentimes when someone is looking to break into the enablement function for the first time they struggle with how to demonstrate applicable skills, but the truth is the skills that make a great enabler can be grown from many different backgrounds!

Here are some key ones I look for:

Customer focus: A demonstrated ability to understand different stakeholder's problems and goals, with examples of where you've taken action to solve those problems.
Strong communication skills: An enabler must be able to translate programs and strategies across teams.
Measurable impact: Enablers must be able to translate their programs into measurable impact for the teams they support, so I look for candidates who think beyond their tasks to how their work impacts the organization and the broader team.

Q: “When evaluating potential candidates for sales enablement roles, what are the qualities or attributes that you consider most important, beyond what's typically found on a resume?"

A: When I'm interviewing enablement candidates I look for a few key things:

Communication skills: Many enablement candidates come from sales or customer-facing backgrounds (I did!) but even if you didn't, sales enablement requires strong communication skills to translate strategies internally and "sell" your strategic impact.
Organizational skills: Whether it says in the title or not, all sales enablement roles require some level of program management, which means candidates must be organized and thoughtful about how they approach their work and deliverables.

Burnout and the fear of being cut

Q: “Burnout is a concern in many high-pressure roles. Can you suggest any strategies on how to avoid/deal with it or any coping mechanisms?”

A: This is such a relevant topic this year! Burnout is real, and in the current economic environment where many companies are looking to cut costs that often means a reduction in resources or headcount for sales enablement teams.

It may mean your team has a broad remit of work to focus on, and you only have partial resources to get them done.

Whatever the case, avoiding burnout is an important thing to think about. I don't believe strategies are one-size-fits-all, but here are some that have worked for me:

Be open with your leadership about how you feel about your workload: If you speak up sooner if you're feeling overwhelmed, the more likely you'll be able to make adjustments before you feel burnt out.
Think about your boundaries: This is a topic I feel is always "easier said than done" but for me, it means thinking about what things outside of work are non-negotiable for you. Maybe it's having time to work out, spending time with family in the evenings, or leaving early on Friday afternoons so you can go camping for the weekend. Whatever your priority is, don't compromise on it. No matter how full your plate is at work and how much you need to do, make time for those non-negotiable things.
Keep track of your impact: When you're working on a big project, make sure you have written somewhere what the impact of the work is and why it matters. This will not only help you speak up to your leadership about your work, but it will help you stay anchored to why it matters and try and block out some of the other noise that comes in.

Q: “Sales enablers always feel the pressure that they will be the first team to get the boot if there are budget cuts, how to control the situation and stop this fear from developing?”

This is a very real fear, and unfortunately often a reality, so thank you for the question!

The most protective measure sales enablement teams can take is to ensure leadership at the highest levels of the organization understands the value that your team is creating and how it directly impacts business outcomes.

Often this knowledge of impact can be held at the sales leadership or marketing leadership level, but if the C-suite at your company doesn't know how important your work is to the successful growth of revenue then make sure you find an opportunity to make that known!

Also, if you feel your company is feeling the pressure for performance and growth, make sure you're having constant conversations with your stakeholders about what their key priorities are and how you can best support them.

The more nimble you can be to adjust to shifting business priorities the better.

For example, in crunch times companies often stop or slow down hiring and onboarding, which can mean shifting resources away from recruiting and enablement.

So make sure you and your team are nimble and can quickly show value outside of new-hire training and onboarding, and support the existing sales team in other ways too.

Moving from reactive to proactive enablement

Q: “What advice do you have for teams that are in a reactive state of enablement (putting out fires)? What are the steps to become a proactive function that is strategically planning ahead instead of just jumping from one initiative to the next?

A: This is absolutely a hard swap to make as enablement is typically a function that is under-resourced, and different leaders have different ideas on how to best leverage their enablement teams.

I would say step one would be to sit down with your stakeholders to understand what their top priorities for your enablement team are and see if stakeholders are in alignment or if they have differing opinions.

Then, create a roadmap of all the priorities discussed, and compare those priorities to the current bandwidth of the team.

If the team is only focusing on reactive enablement tasks, this exercise will identify the other key priorities they’re missing.

The more open dialogue you can have with your leaders and stakeholders about ruthless prioritization of your work, the more likely that you'll be able to free up some bandwidth for proactive strategic planning, which means that some other priorities might have to get backlogged!

I recommend making this prioritization exercise a quarterly occurrence and then throughout the quarter keeping your stakeholders in the loop about how you're progressing toward your strategic priorities.

What sets senior enablers apart and how to develop in your role

Q: “I’d be curious to know what you think is the biggest thing that sets a junior enabler apart from a more senior one. And what should people in junior roles do in order to stand out and reach the heights of their senior peers?”

A: In my experience, the more junior enablers I've worked with are focused on task-based roles, executing important enablement functions and projects, and supporting more senior enablers.

These tasks are crucial to a successful enablement team, but can often go under-appreciated compared to some of the more obvious enablement impacts. If you're looking to grow in enablement here are some steps you can take:

If you're lucky enough to work on a team with a talented senior enabler, ask them to be your mentor! Tell them you're interested in growing your career and skill set, and ask them if you can shadow them on some of their bigger projects. For example, if you have a senior person on your team working on a new training program, ask if there's something more you can take on in the project above what you normally would.
Make time in your 1:1 meetings with your manager to be explicit about your desire to grow. Ask for specific feedback from your leader about where you have opportunities for growth, and if they have advice on what skills you should be working on to achieve that growth. If possible, try and set a workback plan for growth goals. For example: "I would like to be promoted to senior enablement manager next year, what steps can we take together between then and now to make that a reality?"
Lean on cross-functional partners to be your advocates! Strong peer feedback can be an important part of moving forward in an enablement role, so make sure your stakeholders know that you want to grow and that you're open to feedback on how to best get to the next level. If you can, find a friend or colleague who can be your cheerleader - who’ll shout you out when you accomplish something great and make sure your work or impact is known.

Q: “As a Sales Enablement Manager, I'm keen on furthering my career in this field. Are there any skills or areas of expertise that I should focus on that you would recommend to advance to a more senior role in sales enablement?”

A: The more senior you grow in an enablement function, the more your focus shifts away from executing programs and towards strategic outcomes for your organization's revenue growth.

For example, as a junior enabler, you may have KPIs set around developing a new program, rolling out a new training program, or delivering X, Y, and Z.

As a senior leader, your KPIs will be more tied to organizational outcomes, such as reducing seller time to first sale, improving sales team win rates, and measurable operational efficiency outputs.

One area I would recommend growing your skills in to best prepare you for a more senior role is business analytics. Make sure you're familiar with your organization's success metrics, how they're trending, and how to leverage them to communicate your team's impact on success.

Q: “What advice do you have for someone new wanting to grow and level up in their role? What are the steps to go from taking marching orders to proactively taking on new challenges and making an impact?”

A: The fact that you are asking for opportunities to take on new challenges and level up your impact is already a key step towards growth.

"To ensure my team stays focused on growth opportunities, I ask my direct reports to tell me about items of current work as they come up and to save pressing conversations for our 1:1s. This way we can work on them together in real-time, and nothing gets lost in the preceding week."

This means our weekly 1:1 time doesn't get taken over with tactical work items, and instead is protected time to talk about growth opportunities and career goals.

I'll ask questions like:

What is the thing you're working on right now that you most enjoy?
What is the thing you're working on that you least enjoy or that drains you?
What is our team working on right now that we should focus on less, what should we focus on more?
What is the main skill you'd like to help improve on this quarter?

These questions allow me and my team to keep our conversations forward-looking and make sure our feedback is flowing both ways.

I'd recommend thinking about how you prepare for your 1:1 meetings with your leader to make sure you're taking full advantage of that time to discuss your growth opportunities.

Q: “What would you recommend if your company does not offer reimbursement for external training/certifications/conference attendance/memberships and the costs to do all of the above are beyond what you can afford?”

Great question! Certifications and conferences are certainly a great way to grow your enablement skills and network, but fortunately, there are also some free resources available if your company will not reimburse you.

LinkedIn Learning is free if you have a library card in most areas! You can get a library card for free to gain access to a lot of free coursework, and you can then add a tag to your LinkedIn profile to show the effort your putting in to continuous learning
Join a free networking group like Upnotch and Sales Enablement Collective to meet other sales enablement professionals to level up your skills and grow your network. Shout out to the SEC newsletter that Harshil Boparai (SEC’s Community Manager!) sends out with lots of regular sales enablement content.
Check out podcasts (like SEC’s own Sales Enablement Innovation podcast!)
With your library card, you can download the Libby app to check out digital copies of books that can help level up your enablement skills

Networking for enablement and navigating office dynamics

Q: "Building a career in sales enablement often involves networking and it's quite daunting, to be honest. What are your tips for effective networking, and how can professionals use our network to advance our careers?”

A: Networking absolutely can be daunting, and my biggest fear when networking is to have the person I'm speaking to feel like I am at all wasting their time, so I would say my main tip for effective networking is to be prepared!

What do you hope to get out of the conversation? Use that goal to come prepared with a few key questions, and be prepared to be transparent about your goal with the person you're networking with.

Looking to land your next job? Tell them!

Just looking to learn more about how they grew their career and learn? Tell them!

Hoping to get some advice on your career path? The more open you are about your goals the better. People want to help!

Also, I'd like to plug organizations like Upnotch, which connect people who have overlapping networking goals to find mentors. They also hold "speed networking" events that I find are great icebreakers and make new connections in a structured space, helping you build confidence in networking.

Networking in sales enablement is really important, because it's still a growing function, so the more you know about enablement at different organizations and what makes other enablement professionals successful, the better.

💡

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Q: "Something I've been struggling with lately has been navigating the complex landscape of office dynamics, particularly in regards to a larger organization. What insight can you offer for professionals in sales enablement to successfully build cross-departmental alliances and foster positive relationships with various teams, all while managing office politics?”

A: Cross-functional relationships are key to success in sales enablement so this is an excellent topic! Here are a few points to share:

Make time intentionally to build rapport with cross-functional stakeholders. Whether you're in the office, hybrid, or fully remote, intentionally reach out to your stakeholders across the organization just to check in, don't only go to them when your work dictates you need to or when you have a question for them. Being seen as "easy to work with" can be a big unlock for enablement success.
Find stakeholder champions. If you're struggling with office politics between teams, try to find one leader on both of the teams that can be your advocate. Is there a revenue leader who can help you navigate the office political waters? Can they help bridge connections cross functionally?

In my experience, asking my revenue leaders for advice on how to navigate tough conversations with stakeholders in different parts of the organization has paid dividends. They can probably help in ways you didn't think of!

Finding more AMAs and sales enablement content

First of all, another big thank you to Alicia for taking the time to answer the sales enablement community’s questions.

If you want to ask a question of your own next time we host one of our regular "Ask Me Anything" sessions, all you have to do is join our free Slack community.

You’ll join thousands of your sales enablement peers in a space where you can network, share content, ask questions, and stay up to date with all the latest in the space.

What’s not to like? Join the community for free today.