I shall work with the assumption that the base field is any field $K$. Let $V:=\text{Mat}_{n\times n}(K)$. Suppose that $A_1,A_2,\ldots,A_k\in V$ are such that $A_i^2=1_n$ for every $i\in[k]$, and $A_iA_j+A_jA_i=0_n$ for all $i,j\in[k]$ with $i\neq j$. Here, $1_r$ and $0_r$ denote, respectively, the $r$-by-$r$ identity matrix and the $r$-by-$r$ zero matrix, and $[m]:=\{1,2,\ldots,m\}$ for all $m\in\mathbb{Z}_{>0}$.
First, we handle the case where $K$ is of characteristic not equal to $2$. It has been shown that, if $k>1$, then $A_i$ and $-A_i$ are similar matrices for all $i\in[k]$. That is, if $k>1$, then $$\det(A_i)=\det(-A_i)=(-1)^n\,\det(A_i)\,,$$ making $(-1)^n=1$, whence $n$ is even. Thus, if $n$ is odd, then $k\leq1$. From now on, we assume that $k>1$ and $n$ is even.
Consider the linear operator $T_X:V\to V$ defined for each $X\in V$ by
$$T_X(Y):=XY+YX\text{ for any }Y\in V\,.$$
If $X$ is diagonalizable over $K$, then let $x_1,x_2,\ldots,x_n\in K^n$ be eigenvectors of $X$, with respect to eigenvalues $\lambda_1,\lambda_2,\ldots,\lambda_n\in K$, respectively, and let $\chi_1,\chi_2,\ldots,\chi_n\in K^n$ be eigenvectors of $X^\top$, with respect to eigenvalues $\lambda_1,\lambda_2,\ldots,\lambda_n\in K$, respectively. Then, the $n^2$ linearly independent matrices $x_\mu\,\chi_\nu^\top$ are eigenvectors of $T_X$, with eigenvalues $\lambda_\mu+\lambda_\nu$, for $\mu,\nu\in[n]$.
Without loss of generality, we suppose that
$$A_1=\begin{bmatrix}+1_{\frac{n}{2}}&0_{\frac{n}{2}}
\\0_{\frac{n}{2}}&-1_{\frac{n}{2}}
\end{bmatrix}\,.$$
Then, $A_1$ is diagonalizable with eigenvectors $e_1,e_2,\ldots,e_{\frac{n}{2}}$ corresponding to the eigenvalue $+1$, and with eigenvectors $e_{\frac{n}{2}+1},e_{\frac{n}{2}+2},\ldots,e_n$ corresponding to the eigenvalue $-1$. Here, $e_1,e_2,\ldots,e_n\in K^n$ are the standard basis vectors of $K^n$. This shows that the nullspace of $T_{A_1}$ is of dimension $2\left(\dfrac{n}{2}\right)^2=\dfrac{n^2}{2}$, since it is spanned by $e_i\,e_j^\top$ and $e_j\,e_i^\top$ with $i\in\left\{1,2,\ldots,\dfrac{n}{2}\right\}$ and $j\in\left\{\dfrac{n}{2}+1,\dfrac{n}{2}+2,\ldots,n\right\}$. Thus, from David C. Ullrich's answer, $A_2,A_3,\ldots,A_k$ are linearly independent element of $\ker\big(T_{A_1}\big)$, so we get $$k-1\leq \frac{n^2}{2}\text{ or }k\leq \frac{n^2}{2}+1\leq \frac{n(n+1)}{2}\,.$$
I however believe that the maximum possible value of $k$ is at most $\dfrac{n^2}{4}+1$.
If $K$ is of characteristic $2$, then clearly the matrices $A_1,A_2,\ldots,A_k$ need to only commute. There is no bound on $k$ (for example, $A_1=A_2=\ldots=A_k=1_n$ works). However, if we demand that $A_1,A_2,\ldots,A_k$ be linearly independent, then a bound for $k$ can be determined. First, we may assume that $A_1,A_2,\ldots,A_k$ are upper triangular matrices each of whose diagonal entries is $1$. Then, $A_2-A_1,A_3-A_1,\ldots,A_k-A_1$ are strictly upper triangular matrices. The subspace of $V$ composed by strictly upper triangular matrices is of dimension $\dfrac{n(n-1)}{2}$. That is,
$$k-1\leq \frac{n(n-1)}{2}\text{ or }k\leq \frac{n(n-1)}{2}+1\leq \frac{n(n+1)}{2}\,.$$ I conjecture that, with the extra assumption that the matrices $A_1,A_2,\ldots,A_k$ be linearly independent, $k\leq\left\lfloor\dfrac{n^2}{4}\right\rfloor+1$.