The end of the year often arrives with a flurry of activity — and for salespeople, closing out Q4 can include an extra-lengthy to-do list.
While everyone is making holiday plans, participating in local festive traditions and ironing out their New Year’s resolutions, sales representatives have the added tasks of closing essential deals during a typically difficult time of year to sell. As year-end quotas loom large, the pressure to perform is on the shoulders of sales teams to get deals across the finish line before New Year’s Day.
While no two products — and therefore, no two sales teams — are the same, many sales organizations aim for a robust, supportive sales culture to help reps perform at their best during the busiest times of year. Regular training sessions, sales enablement programs and forums for customer feedback keep salespeople knowledgeable and confident, and incentive bonuses and recognition programs, such as a President’s Club, affirm high-performing reps as valued members of the team.
The result of these sales team programs is often a spirit of collaborative competition, where reps regularly acknowledge each other’s individual accomplishments and support each other with a team mindset. According to HubSpot’s 2024 State of Sales Report, the highest-performing teams prioritize a trusting, one-for-all approach to culture that lower-performing teams often ignore.
Built In caught up with eight sales professionals to discuss what the end-of-year experience is like for their sales team, what strategies they lean on to stay on target and the advice they have for other sales reps looking for motivation during strenuous times.
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Toast offers SaaS resources to restaurants of all sizes through its all-in-one platform that covers point-of-sale, payments, supplier management, digital ordering, marketing and team management.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
The emerging markets team was formed to address a vast target market in the restaurant industry with English as a second language or other language preferences. The team serves customers in Spanish, Mandarin and Korean. We are helping these restaurants leverage modern technology to boost their businesses and grow.
End-of-year targets are met through preparation and planning. We set realistic goals weekly that will feed into our annual goal. We plan at the beginning of the month and estimate our wins for each week. Preparation comes from our analysis of the pipeline, creating new opportunities and moving prospects through the sales funnel.
To help meet our goals towards the end of the year, we leverage special end-of-year sales promotions, customer referrals, Toast’s competitive advantage and ambitious prospects. It is important to use internal resources to be informed and prepared to win customers against our competitors. For budget-friendly buyers, it’s helpful to use promotions. In terms of highlighting Toast’s competitive advantage, I like to introduce the Toast ecosystems, which allow customers to maximize efficiency and grow their revenue.
How does Toast support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
Toast motivates employees by cultivating a “One Team” mentality. This is one of our core values, and it means we lead with empathy, treat one another with respect and work together. Managers remind us of our goals and create paths to success. Toast keeps us engaged throughout the process by celebrating our wins and cheering us on.
One way we stay motivated throughout the year is through sales competitions and sales performance incentive funds — or SPIFFs. Each quarter, there’s a different theme. The friendly competition amongst the team keeps us all motivated, even during slower months.
“The friendly competition amongst the team keeps us all motivated, even during slower months.”
What sort of celebrations does your team have for salespeople who hit their quotas?
On the emerging markets team, we give shoutouts to one another on team messaging channels and celebrate each other’s successes as a group.
Toast also has a recognition program where you can award “toasts” to one another, which can then be redeemed for gift cards, charitable donations and more. We use “toasts” to congratulate each other and recognize big wins.
Workiva provides a cloud-based connected reporting and compliance platform that helps customers streamline their data and processes.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
Personally, I have a plan for the end of the year by the end of Q2. With the sales cycles that we encounter, we have to be well-prepared going into the last quarter. I start by prioritizing the accounts that plan to close this quarter and any that I think I can pull into the quarter as well. I work closely with my account manager to ensure we are on the same page regarding meetings we need to schedule so we have a strong Q1 as well. We are thinking ahead and planning all the time!
As we approach the final quarter of the year, it’s essential to recognize this period as a prime opportunity for implementing high-impact sales strategies. Historically, Q4 tends to generate heightened purchase intent, as many businesses and consumers aim to wrap up the year with specific goals in mind and budgets to use. By concentrating on tailored promotions, focused lead nurturing and strategic upselling, we can leverage this time to maximize revenue. Effective Q4 planning also allows us to address any gaps from earlier quarters, positioning us strongly as we enter the new year.
How does Workiva support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
Workiva supports us in a number of ways. With clear goals and incentives, we, as salespeople, always know where we need to be at a minimum and most people strive to be ahead of this. This includes both short-term incentives during slower periods and long-term recognition programs like the President’s Club.
We also have ongoing training and development. It’s important that we invest in continuous learning through workshops, coaching and team building throughout the year. I also try to read or listen to a book on professional development each quarter.
We are also always collaborating with and cheering on our teammates. Through team meetings, we can do check-ins, ensure we are all aligned on broader company goals and share best practices.
Lastly, Workiva supports a healthy work-life balance. I don’t think I could do this without the balance that Workiva affords us. I feel that as a high-performing professional, I am given the respect that at the end of the day, I have a job to do, and sometimes my time needs to be prioritized with having a flexible schedule and wellness breaks. These four things enable me to feel supported, valued and inspired to deliver my best, no matter the season.
“Workiva supports a healthy work-life balance. I don’t think I could do this without the balance that Workiva affords us.”
What sort of celebrations does your team have for salespeople who hit their quotas?
We celebrate when anyone hits their annual quota, but the ultimate celebration is the President’s Club, which is earned by the highest-performing people in the organization.
President’s Club is the ultimate sales celebration — a luxurious, all-expenses-paid trip to an incredible destination. It’s more than just a reward; it’s an unforgettable experience shared with amazing colleagues and carefully curated by an exceptional team dedicated to making every moment extraordinary. Once you earn your spot at President’s Club at Workiva, it becomes the milestone you strive for every year — you won’t want to miss it again.
Centerfield delivers outcome-based digital marketing solutions and omnichannel experiences for the world’s leading brands.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
My team does a great job of asking clients what their end-of-year goals are and if they are making a strong push to end the year. The vast majority of marketers and sales teams are in the same position as us each year — needing an extra boost to finish strong and build momentum into the following year. As such, we can uncover incremental spend for current partnerships and even discover new, Q4 initiatives that lead to extra budget. Even if the timing isn’t perfect, our clients know that we have available opportunities just by planting the seed and asking the question!
How do you stay motivated to maintain high performance throughout the year, including during traditionally slower months?
Seasonality is a constant in almost any business. I have a few important pieces of advice to navigate sales velocity through the year.
Know your client’s planning and spending cycles. Are they on a traditional calendar cycle, or are they offset? If it’s the latter, their seasonal pushes and planning motions may take place during otherwise slow periods.
During summer months when vacations cause havoc with scheduling and client or prospect response times, it’s extra important to schedule the next meeting ahead of time. Getting conversations on the calendar prevents getting lost in the shuffle, as most people need a few days just to dig out of their inboxes after their vacations.
Stay process-oriented. You can’t always control the sale, but you can control the activity — prospecting, outreach, meetings, etc. If you know your numbers — for example, your meeting-to-close ratio — each meeting becomes a win with a clear monetary value tied to it.
“Stay process-oriented. You can’t always control the sale, but you can control the activity.”
It’s okay to align your schedule to the slower months as well. Schedule personal appointments on Fridays in the summer when your email is slow and clients aren’t responding. That way, you don’t have to worry about that appointment on a busy Wednesday during the last week of a quarter.
What sort of celebrations does your team have for salespeople who hit their quotas?
Everybody accepts praise a little bit differently. I try to learn how people like to be praised and adjust accordingly. For some, I will extend praise during team meetings in a public forum. For others, I tend to praise privately. As a group, we have a “#Gong” channel on Slack where all wins are posted. Almost always, the entire team reacts with an emoji. It is a simple method, but one that fosters camaraderie.
Of course, all salespeople are motivated by money. We have commission structures with accelerators for exceeding quota, which acts as an added incentive to go above and beyond.
CarGurus offers an all-in-one platform for the car shopping journey, including selling, financing, purchasing and delivery.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
At CarGurus, our monthly sales cycle demands consistent focus, and the final months of the year present unique challenges. With many of our car dealer customers off for the holidays, the sales cycle in November and December is significantly compressed. To stay ahead, we plan to make the most of each day by setting ambitious targets and ensuring our pipelines are active. Knowing that year-end is when long-term plans and budgets are top-of-mind for dealers, we proactively share data and insights to support their decision-making. By highlighting how our products can help them seize emerging opportunities or address challenges, we aim to add value to every interaction. This enables us to meet our targets while laying the groundwork for a strong start to the new year.
How does CarGurus support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
Collaboration is a core value at CarGurus, and it really thrives within our team. People genuinely want to help each other succeed. Our quota attainment rate is very high for sales — in fact, the majority of our team hits their goals each month — significantly more than what’s typical in many organizations.
To keep momentum high, we offer quarterly SPIFFs and host activities that bring the team together to work toward their goals. For example, our monthly “Mid-Month Madness” event gets everyone in the office to make calls and win prizes throughout the day. It’s high-energy and a lot of fun. You feel similar vibes on the last days of each month when it’s common for team members who’ve already hit their quotas to help others achieve theirs. Managers have dedicated budgets to bring teams together outside the office, offering a chance to reflect, connect and recharge in fresh settings.
“Collaboration is a core value at CarGurus, and it really thrives within our team. People genuinely want to help each other succeed.”
What sort of celebrations does your team have for salespeople who hit their quotas?
Recognizing and rewarding hard work is a big part of our culture at CarGurus. We do this informally every day through conversations and updates and more officially with special announcements and events. For example, we host a monthly “Champions Dinner” to celebrate the top salesperson at every level. We also recognize achievements through promotions — about 20 percent of our team has been promoted this year, a testament to the incredible talent and dedication within our group.
In our monthly sales team meeting, we highlight everyone who hits or exceeds their quota and take a closer look at the stories behind some key wins as well as learning moments. It’s a great opportunity for team members to showcase their strategies and share insights to help others succeed. And like many sales organizations, we have an annual President’s Club trip to reward our top reps at each level. Last year, we went to Barcelona! Experiences like these demonstrate our deep appreciation for the team’s hard work and leave them energized to tackle the challenges ahead.
JumpCloud’s Open Directory Platform gives businesses a cloud-based solution for remote IT, security operations and DevOps.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
As we approach the end of the year, we augmented the traditional 13-week quarter to 11.5 and placed a strong emphasis on prioritization and focus. Our strategy involves narrowing down to high-potential leads and accounts to intensify outreach efforts. Managers work closely with reps to review pipelines and key performance indicators, identifying and removing obstacles that prevent day-to-day execution.
We also implement incentive programs, often with a focus on weekly “stretch goals” to encourage reps to push for additional volume. Another effective strategy is aligning with marketing and demand generation to re-engage key prospects and capitalize on any potential year-end budget usage.
How does JumpCloud support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
Maintaining momentum year-round is crucial, especially during slower months like August and September in Europe, the Middle East and Africa and October through December in India. To support consistent performance, we offer ongoing coaching and development for each team member. Managers conduct regular one-on-one sessions with a standardized document that each individual contributor is responsible for filling out that highlights linearity and pacing, goal setting, gap closing if applicable and career progression. We’re also intentional about recognizing high-performers to keep morale high. Additionally, our company fosters a culture of transparency and growth, with open communication on performance metrics, we’re in the process of building career progression paths and opportunities for skill development.
What sort of celebrations does your team have for salespeople who hit their quotas?
We believe that recognizing achievement is key to building motivation and morale. After being at JumpCloud for four months, I’m looking forward to evolving and building upon great programs.
“We believe that recognizing achievement is key to building motivation and morale.”
For those who hit their quarterly quotas, we celebrate both at a team level and companywide. At the end of each quarter, we hold recognition events where top performers are highlighted, and we award certificates or small prizes to acknowledge their hard work. For annual achievements, we provide larger rewards, such as our version of the President’s Club, called the “101 Percent Club.” This is truly unique as a lot of technology companies do not allow the sales development team access to the President’s Club. This illustrates how important the sales development team is and the regard that JumpCloud has for what we deliver to the company. This is truly a company that cares. Lastly, the team also celebrates each other’s wins with peer shout-outs in team meetings and on company communication channels, fostering a supportive environment of shared success.
Snap! Mobile is a software platform for school athletics and activities, helping facilitate fundraising, fan engagement, communications and more.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
In our business, Q4 brings many challenges with the holiday breaks, final exams and the unpredictability of the weather. Staying ahead of forecasting your pipeline and over-communicating expectations to make sure that all targets are met is imperative. With our team selling approach, we can take some of the activation responsibilities away from the sales team and keep their focus on new business and getting ahead of future cycles.
How does Snap! Mobile support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
At Snap, we, like most businesses, have some peak seasonality to our business based on when activation happens with our sales cycle. We have traditionally been able to support and motivate our teammates with different metrics that influence the rest of the year’s pipeline and total revenue that is driven. This is where the best reps separate themselves from the pack with their commitment to daily sales activities and getting ahead of the more traditional heavier workloads.
What sort of celebrations does your team have for salespeople who hit their quotas?
Within our different sales teams, we have many internal prizes, competitions and SPIFFs. Within a sales organization, recognition within your team and company can be measured in multiple ways. Some of this is based on the personality of that individual achiever, what they value and what will motivate them. Building a team goal that aligns with the individual’s goals is the ultimate win-win!
“Building a team goal that aligns with the individual’s goals is the ultimate win-win!”
Analytics8 is a data and analytics consultancy that helps companies stay ahead in a rapidly changing world.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
At year-end, our approach centers around understanding and supporting our customers’ final needs and goals. Our team proactively reaches out to help clients make the most of their remaining budget, finding tailored solutions to address their specific year-end requirements.
We stay data-driven by closely tracking our client's progress through key metrics and adjusting our strategies as needed. This commitment to insight and flexibility keeps us aligned, motivated, and focused on closing each deal in a way that genuinely benefits our clients.
How does Analytics8 support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
Analytics8 ensures consistent motivation and support by focusing on growth, connection and recognition. Throughout the year, including slower months, we’re offered targeted training, achievable mini-goals and frequent check-ins to keep us sharp and engaged.
Managers actively recognize our efforts, valuing both our hard work and our development. Even during quieter times, we’re encouraged to refine our skills, prospect to drive more deals through the pipeline and build relationships — keeping the momentum alive and preparing us for peak periods. This balanced approach keeps us driven, so we’re always ready to perform at our best, no matter the season.
What sort of celebrations does your team have for salespeople who hit their quotas?
We make it a priority to celebrate our quota hitters with meaningful recognition that acknowledges their hard work and dedication, not just their sales numbers. From team shoutouts and personalized awards to social media highlights, we make sure each salesperson’s achievements are truly appreciated.
“We make it a priority to celebrate with meaningful recognition that acknowledges their hard work and dedication, not just their sales numbers.”
Our leadership team adds a personal touch to these celebrations, sharing stories or even bringing in celebrity cameos to give the rest of the company a glimpse into who we are beyond work. With monthly, quarterly, and annual celebrations, everyone gets a chance to honor each other’s successes, building camaraderie and showing genuine appreciation for every milestone achieved.
Dscout is an experience research platform that helps customers gather, manage, share and analyze content.
How does your sales team approach the end of the year to ensure targets are met? What strategies are most effective during this period?
Dscout is exceptionally supportive from the top down within the sales organization and the cross-functional teams. Since we are near the finish, there is more clarity on what needs to be done to get across the line. Weekly forecasting and deal review calls are already in place to provide transparency into active opportunities and pinpoint where help is needed.
Frequently, the end of the year offers mutual motivation for our customers and ourselves to get contracts wrapped up before the end of the year to align with budgets and be ready for the new year. With that in mind, our team will establish weekly syncs with the customer to provide dedicated time and attention toward completing the deal on time. We will also proactively plan for any inevitable time away during the holidays to minimize any surprises or delays while showing a high level of empathy for time off during this period.
How does Dscout support and motivate employees to maintain high performance throughout the year, including during traditionally slower months?
Support and motivation for high performance is a continuous motion at Dscout. Every time a teammate wins a deal, an automated alert is pushed to our Slack that is visible to the company, and everyone rains congratulatory emojis and responses to celebrate the accomplishment mutually. The salesperson will often provide details on what it took to get across the finish line and give shout-outs to different people across the company. The encouragement and celebrations help keep the sales energy high and motivate everyone to keep pushing forward.
“The encouragement and celebrations help keep the sales energy high and motivate everyone to keep pushing forward.”
One of the best pieces of advice we have been given is that slow months are due to slow prospecting in the prior months, so we are encouraged to prioritize prospecting and top-of-funnel activity, even during busy times.
What sort of celebrations does your team have for salespeople who hit their quotas?
Celebration and recognition of sales excellence is a cherished part of being at Dscout. Our CEO and leadership team will highlight the achievement in company-wide Slack and at our monthly all hands meeting. The recognition is also re-iterated across the sales team during quarterly team reviews, adding a personal touch to each recognition. Sales leadership will also treat the salesperson to a nice dinner or send meal credits if the person is remote, showing our appreciation in a real, tangible way, and further emphasizing individual achievement in our recognition process.
