Wisetack’s Iris Pfeifer On How To Turn A Good Sales Team Into A Great One
A strong, high-performance sales team is critical to a successful business. But what makes a sales team truly great, and what strategies can leaders use to create a team that's highly successful? To address these questions, we're talking to CROs and sales executives about "How To Turn a Good Sales Team into a Great One." As a part of this series, I had the pleasure of interviewing Iris Pfeifer.
Thank you for doing this with us! Our readers would love to learn a bit more about you. Can you tell us what brought you to this career path?
After college, I didn’t necessarily know I wanted to work in startups. I had a positive experience interning at Nextdoor when it was a pre-launch startup of just 30 people, but I didn’t really have an incredibly strong sense of what path I wanted to take. In fact, my undergraduate course of study had essentially nothing to do with tech or business at all.
Through some connections I made in college, I was able to navigate into a product manager role after graduation for an early stage startup, TalentSky. That included everything from shadowing customer meetings to building product specs. I learned that I really loved talking to customers and figuring out how to create value for them.
I then joined a company that is well known now, but at the time no one knew: Affirm. I was part of the early go-to-market team. I remember we’d send out emails talking about Buy Now Pay Later and people would send back angry responses or just flat out ignore us. It was like that for a long time. Affirm taught me a ton about how to craft a value proposition that actually resonated with customers, and how to work with internal technical teams to build a product that actually resonated with the market.
Next, I joined Carta, an equity management software platform. The company had just undergone a new brand name and, even though there were a few hundred employees, were really just starting to build structure into their marketing efforts. I started in sales and moved into marketing because I was motivated to learn another function. I worked under a marketing leader who taught me so much about what an excellent marketing function looked like: ensuring high quality standards for everything we released, moving quickly, strong goal setting and ruthless prioritization, to name a few. I loved how fast we moved in that environment, and how people were empowered to stretch their skill sets.
Joining Wisetack wasn’t necessarily part of a master plan, but it did really bring all my past experiences across product, sales and marketing together. I knew I was passionate about early stage companies, and that I wanted to go to a place with an experienced, strong founding team; strong venture backing; early product market fit, with lots of room for rapid growth; and, a perhaps less tangible 'sense of belonging.' In other words, would the team trust me and believe in me? Wisetack met all of those criteria and more. So, on the week pandemic lockdowns were going into effect, I said yes to being employee number 10, and took on the challenge of building out the sales and marketing functions.
Can you share an interesting or amusing story that has occurred to you in your career so far? What did you learn from it?
I met the Wisetack team in the first quarter of 2020, and got an offer the week the country was shutting down at the start of the pandemic. Literally, the reason it took longer than expected to get my written letter was because they were evacuating all the international engineers, who had been in town that week for a company meeting. I later learned that some of them got the very last flights back to their home countries in South America and Eastern Europe.
At that time, I was so excited about the prospect of joining a promising early stage company, but in late March of 2020 the decision suddenly felt riskier. No one knew how the pandemic would change the world. Many tech companies were bracing for hard times, and investors were describing it as a Black Swan event. But I realized that while I might be taking a chance, in some ways it was less risky than staying at a big company. Wisetack was (and remains) well-funded and led by effective leaders, with room for the business to have an amazing trajectory. So, while at face value, being at an early stage can be risky, it actually had a lot of sound fundamentals which de-risked it a lot.
To the point about not being able to predict how it would change the world, I’d interviewed in this small shared office space, not comprehending that I’d never actually set foot in it as an employee. I spent most of my first year connecting with coworkers over Zoom and hikes scheduled between COVID variants. I built a team that was mostly distributed when I’d previously had a strong bias for hiring folks in the Bay Area. But it’s all working. The company has been successful and my experience has been incredible.
Finally, I think there is something to be said for the fact that there’s often never a 'perfect' time to take a calculated risk. And this was one that I was really excited to take.
Are you working on any exciting new projects now? Tell us about it!
We uncovered some issues with the goals we’d set for 2022, so we’ve spent a lot of time reworking them for 2023. Essentially, we were hitting our signings or logos goals, but the types of deals we were signing weren’t all perfectly aligned with the type of growth we actually want as a company. I believe that most effective sales teams can figure out how to hit their goals, but sometimes the way the goals are stated might be problematic. For example, goals that focus too much on signings and place no emphasis on retention, usage, or implementation might mean you’re generating short term wins that don’t stick.
So we put new goals in place that (hopefully) emphasize the right things, and invested in putting all the reporting and measurement in place to give the team visibility on performance. I think this will align our team’s time to creating value for the business.
As part of this, we recognized an opportunity to build an additional go-to-market motion to augment our existing strategy of embedding our fintech products into SaaS companies. We created new roles, goals, and essentially spun up a new team in support of this. I’m so optimistic about the impact they’ll have on our business. It was also really cool to open up professional growth opportunities for existing members of the team who’ve contributed so much already.
None of us can achieve success without some help along the way. Is there a person you're grateful for who helped to get you where you are?
My husband. We have had similar roles over the last five to seven years at similar types of companies. This means we have been able to learn from each other. Oftentimes we’ll spend our Saturdays talking about a business problem and brainstorming ways to solve it. I know this isn’t for everyone, but when we’re really engaged in our work to the point that we want to discuss it on weekends, it basically unlocks all this extra time and brain power going into problem solving. It’s definitely been a force multiplier in terms of making me effective in my work.
Can you tell us a bit about your experience leading sales teams? How many years of experience do you have, and what size teams?
I have completely focused my career on early stage go to market. For me, that’s the most exciting and energizing part of building a company: you have a product, you have demonstrated potential with a small number of very enthusiastic customers, and then the question becomes, how big can we become, and how quickly. I have spent nearly a decade being on, building, and leading teams that are in the stage where you’re not talking about 20% year over year growth, but 3x, or 10x YoY growth, and that really energizes me. These teams have been as small as 1 (just me! When I joined Wisetack) and as big as 30-40. Much bigger than that, it’s a really different dynamic, and frankly, outside the scale where I feel like I am uniquely positioned to make a difference.
What do you think makes a sales team great? What strengths or characteristics do you try to cultivate?
Find the 80-20 rules. In other words, where can 20% of your effort generate 80% of the results? I think people who have good instincts can be game changers in environments where you have limited resources, and need to prioritize ruthlessly. This is one reason where I’ve seen folks with management or strategy consulting experience shine. Anyone who’s worked with me knows I have a bias for teams with diverse backgrounds, and I love giving folks with non-traditional or non-sales backgrounds a shot.
Be really smart and think critically. Early stage growth indexes heavily on problem solving. How can a basic product fit a customer's complex set of needs? How can you position yourself as the most attractive solution possible? How can you understand your customers better?
Finally, collaboration! This is a reason why I sometimes like to ignore traditional sales metrics, which focus a lot on individual success. In reality, the company will only be successful if smart people collaborate and share their learnings to make everyone better, including folks outside of sales. To facilitate this, we push for as much transparency as possible, including pipeline update meetings focused on generating ideas and problem solving instead of just updates; Slack updates in public channels on deal progress (and headwinds!), documenting deal decisions and progress in detail in Wikis, and having reps tag-team deals instead of running with each deal solo.
As with any department, there can be a lot of different strengths, weaknesses, and personalities. How do you manage such diversity on an individual basis? Is there such a thing as a blanket motivator?
Just understanding these differences is half the battle. As a manager, you have to take the time to understand each person’s motivators, near- and longer-term goals. If a person doesn’t have clarity on their goals, as a manager, one of the best things you can do is help shape their goals. Once you’re aware of unique strengths, weaknesses, goals, and personalities, you can manage to those more effectively.
All that said, I don’t think there are blanket motivators, but a very common one at my company is that everyone on my team is united around making the company successful. I believe that for people who joined when the company was less than 100 people, the biggest way they can grow their careers is by being formative to the company’s long term success. This plays out in terms of earning potential as well as career growth. It will open doors for so much in the future. When I think about folks who were high-impact early employees at successful startups, they seem to have almost limitless doors open.
On the flip side, I actively avoid putting too much weight on monetary incentives. The folks we have who are having the biggest impact aren’t motivated by those anyway. In some cases, they feel it actually cheapens the work they do (trust me, I was surprised to hear this feedback). They care more about building a company that is 10x, or 100x more valuable than we are today.
I also think this is unique to our company stage. When you’re talking about motivating a sales org of 100 people, it’s a different story.
What strategies have you tried to increase motivation, engagement, and productivity? We want to hear it all; the stranger, the better!
- Offsites, like a revenue kickoff event, training summit, or teambuilding activity
- Adding multipliers on specific types of deals to give more credit for deals that drive more value for the business
- Gift cards for knocking out mundane manual tasks
- Productivity happy hours over Zoom
- Tracking engagement via employee NPS, and reviewing the detailed feedback
- Doing probably more 1:1s than we need to do. I just think it’s so, so important to maintain meaningful personal relationships with folks on the teams, and to get feedback as proactively as possible. To this effect, I also encourage my direct reports to do skip-levels, which is meeting with leaders above me, including our CEO.
Of all the strategies you've tried, which did you find to be most effective? How did this have a direct correlation to sales?
We’re remote-first right now, so whenever we can bring people together, it energizes and motivates the team. This has been true of team offsites, as well as offsites with key customers and partners. Even marketing events and tradeshows are a good option.
We invested in these as the pandemic eased because they felt like an important way to solve problems, train the team, and drive projects forward, but they had the unexpected impact of energizing and motivating teams. I guess it makes sense that after sitting with a customer or coworker and understanding a lot more about their pain points, you come back with ideas about how to solve their problems, and a stronger emotional investment in making things better for them.
The effectiveness has shown up in our time to implement and time to go-live. These in-person sessions seem to move the needle most in areas where having a joint roadmap or joint execution plan makes a difference, and it’s post-deal signing where we see the bulk of that impact.
Can you tell us about a time your sales team outperformed their targets? How high over did they go, and what was that like for everyone?
Last spring and summer were really fun for this reason. We were more than 30% ahead of our targets. This is because our business has some seasonality, and a lot of times, the effort we put in in the slower seasons don’t show results until the summer. I loved that the results of all the effort and dedication from throughout the team showed at once. It was like all the thoughtfulness and teamwork across sales, marketing, and partnerships came together beautifully, and shone through in a big way in our numbers.
Great things often take time. What do you think is a realistic timeline to take a sales team from good to great?
Six to twelve months, sometimes more, and that timeline depends on the profile of the customer and deal cycle. This is the time it takes for the full sales + success motion to fire on all cylinders. I think if you were just talking about new logo signings in an SMB sales cycle, you could probably see measurable improvement in three months.
I think a huge mistake that leaders make is not having realistic expectations on this.
All that said, what are your five strategies that will help turn a good sales team into a great one? Please share a story or example for each.
1 . Encourage collaboration: collaborate early, usually earlier than you’re really comfortable. Don’t wait for perfection to get feedback. For big or complex projects, it can even be useful to collaborate at the earliest stages of defining a project and its desired goals or outcomes. Also, collaboration is more than just getting feedback. It’s involving others in a meaningful way and delegating out portions of a workstream
2 . Be smart: think critically and creatively vs. relying on a playbook. So much about creating successful outcomes has to do with problem solving in unique or complex situations. For example, when entering a new segment or new market, the folks who do this most effectively are those who acknowledge the challenges and risks but more importantly, figure out how to solve them.
3 . Identify the 80-20 rule: this “rule” refers to the phenomenon where 80% of your results come from 20% of your efforts. Nowhere is that truer than in a startup when you’re trying a lot of different tactics and figuring out what works. I’ve seen this to be the case in both sales and marketing—in terms of where you spend your time on your pipeline (sales), and what campaigns you prioritize (marketing).
4 . Be mindful of the difference between horizontal vs vertical product market fit and the team structures that support each strategy. Vertically-focused companies have to go continually deeper into the vertical and/or move to adjacent ones, so there are outsized benefits of collaboration, and having longer tenured reps with deep expertises and leaner teams.
5 . Facilitate strong relationships and create room for FUN. In my first year or two at Wisetack, a lot of the work was a sprint. There were a million things to do and not enough people to get them done, so our effectiveness came down to grinding, and finding every possible minute in the day to make progress. As the team has grown, I now understand the need to create something more sustainable, and also, that most personalities do not derive meaning or joy out of a pure grind. To help people feel connected to our mission, work, and culture, you must create time and space for joy.
Lastly, you're a person of enormous influence. If you could inspire a movement that would bring a great amount of good, what would that be? You never know what your idea can trigger!
I would inspire a movement around helpfulness. I think organizations and people are more effective when we focus on being helpful, or of service, to others—to our customers, to our coworkers, to those close to us. The people and organizations that emphasize this, have, in my life, been most valuable and most effective.
How can our readers further follow your work online?
Follow me on LinkedIn!